Β-Methylphenethylamine: Difference between revisions

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			{{Short description\|Chemical compound}}
			{{Use dmy dates\|date=April 2015}}
	{{lowercase}}		{{lowercase}}
	{{Drugbox		{{Drugbox
	\| verifiedrevid = ~~443420317~~		\| verifiedrevid = 449584722
	\| IUPAC_name = 2-~~phenylpropan~~-1-amine		\| IUPAC_name = 2-Phenylpropan-1-amine
	\| image = Beta-methylphenethylamine.png		\| image = Beta-methylphenethylamine.png
			\| image2 = Beta-Methylphenethylamine molecule ball.png
	\| width = 200px
			\| drug_name = β-Methylphenethylamine

	<!--Clinical data-->		<!--Clinical data-->
	\| tradename =		\| tradename =
	\| pregnancy_category =		\| pregnancy_category =
	\| legal_status = ~~Uncontrolled~~		\| legal_status =
			\| legal_US = Unapproved "New Drug" (as defined by 21 U.S. Code § 321(p)(1)). Use in ]s, ], or ] is unlawful; otherwise uncontrolled.<ref>{{Cite web \|date=February 22, 2023 \|title=BMPEA in Dietary Supplements \|url=https://www.fda.gov/food/dietary-supplement-ingredient-directory/bmpea-dietary-supplements \|access-date=June 9, 2023 \|website=]}}</ref>
	\| routes_of_administration =		\| routes_of_administration =

	<!--Pharmacokinetic data-->		<!--Pharmacokinetic data-->
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	\| metabolism =		\| metabolism =
	\| elimination_half-life =		\| elimination_half-life =
	\| excretion =		\| excretion =

	<!--Identifiers-->		<!--Identifiers-->
	\| ~~CASNo_Ref~~ = {{cascite}}		\| CAS_number_Ref = {{cascite\|correct\|PubChem}}
	\| CAS_number =		\| CAS_number = 582-22-9
	\| ATC_prefix =		\| ATC_prefix = none
	\| ATC_suffix =		\| ATC_suffix =
			\| UNII_Ref = {{fdacite\|correct\|FDA}}
			\| UNII = 6XL7O3V13L
			\| ChEMBL = 158578
			\| ChEBI = 229522
	\| PubChem = 11398		\| PubChem = 11398
	\| DrugBank_Ref = {{drugbankcite\|correct\|drugbank}}		\| DrugBank_Ref = {{drugbankcite\|correct\|drugbank}}
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	<!--Chemical data-->		<!--Chemical data-->
			\| C=9 \| H=13 \| N=1
	\| chemical_formula = C<sub>9</sub>H<sub>13</sub>N

	\| molecular_weight = 135.21 g/mol
	\| smiles = NCC(c1ccccc1)C		\| smiles = NCC(c1ccccc1)C
	\| InChI = 1/C9H13N/c1-8(7-10)9-5-3-2-4-6-9/h2-6,8H,7,10H2,1H3
	\| InChIKey = AXORVIZLPOGIRG-UHFFFAOYAK
	\| StdInChI_Ref = {{stdinchicite\|correct\|chemspider}}		\| StdInChI_Ref = {{stdinchicite\|correct\|chemspider}}
	\| StdInChI = 1S/C9H13N/c1-8(7-10)9-5-3-2-4-6-9/h2-6,8H,7,10H2,1H3		\| StdInChI = 1S/C9H13N/c1-8(7-10)9-5-3-2-4-6-9/h2-6,8H,7,10H2,1H3
	\| StdInChIKey_Ref = {{stdinchicite\|correct\|chemspider}}		\| StdInChIKey_Ref = {{stdinchicite\|correct\|chemspider}}
	\| StdInChIKey = AXORVIZLPOGIRG-UHFFFAOYSA-N		\| StdInChIKey = AXORVIZLPOGIRG-UHFFFAOYSA-N
			\| density = 0.93
			\| boiling_point = 80
			\| boiling_notes = (at 10 mm Hg)
	}}		}}

			'''β-Methylphenethylamine''' ('''β-Me-PEA''', '''BMPEA''', or '''1-amino-2-phenylpropane''') is an ] of the ] class, and a ] of the drug ], with which it shares some properties. In particular, both amphetamine and β-methylphenethylamine are human ] agonists.<ref name="pmid17038507">{{cite journal \| vauthors = Wainscott DB, Little SP, Yin T, Tu Y, Rocco VP, He JX, Nelson DL \| title = Pharmacologic characterization of the cloned human trace amine-associated receptor1 (TAAR1) and evidence for species differences with the rat TAAR1 \| journal = The Journal of Pharmacology and Experimental Therapeutics \| volume = 320 \| issue = 1 \| pages = 475–485 \| date = January 2007 \| pmid = 17038507 \| doi = 10.1124/jpet.106.112532 \| quote = The effect of β-carbon substitution on the phenylethylamine side chain was also investigated (Table 3). A β-methyl substituent was well tolerated compared with β-PEA. In fact, S-(–)-β-methyl-β-PEA was as potent as β-PEA at human TAAR1. \| s2cid = 10829497 }}</ref> In appearance, it is a colorless or yellowish liquid.
	'''β-Methylphenethylamine''' ('''β-Me-PEA''') is a ] ] of the ] ] that is related to ] (which is α-methylphenethylamine). It is found in many '']'' species{{Fact\|date=March 2009}}, notably '']'' (guajillo)<ref></ref>. β-Me-PEA is ] in humans as the β-] ] slows ] by the ] ] (MAO).{{Fact\|date=March 2009}}

			Relatively little information has been published about this substance. Hartung and Munch reported that it had good ] (pressor) activity in experimental animals, and that it was orally active. The MLD (minimum lethal dose) for the HCl salt was given as 500 mg/kg (rat, s.c.) and 50 mg/kg (rabbit, i.v.).<ref name = Hartung>{{ cite journal \| vauthors = Hartung WH, Munch JC \| title = Amino alcohols. VI. The preparation and pharmacodynamic activity of four isomeric phenylpropylamines \| journal = J. Am. Chem. Soc. \| year = 1931 \| volume = 53 \| issue = 5 \| pages = 1875–9 \| doi = 10.1021/ja01356a036 }}</ref>

			A study by Graham and co-workers at the Upjohn Co., comparing many β-methylphenethylamines substituted on the benzene ring showed that β-methylphenethylamine itself had 1/700 x the pressor activity of ], corresponding to ~ 1/3 the potency of amphetamine. The β-methyl compound also had ~ 2 x the broncho-dilating power of amphetamine (as measured using the isolated rabbit lung), and an LD<sub>50</sub> of 50 mg/kg (rat, i.v.).<ref>{{ cite journal \| vauthors = Graham BE, Cartland GF, Woodruff EH \| title = Phenyl propyl and phenyl isopropyl amines. Changes in pharmacological action on substitution of phenyl nucleus and amino nitrogen \| journal = Ind. Eng. Chem. \| year = 1945 \| volume = 37 \| issue = 2 \| pages = 149–51 \| doi = 10.1021/ie50422a010 }}</ref>

			==Synthesis==
			β-Methylphenethylamine can be made by the ] ] of 2-phenylpropionitrile with ] in pure anhydrous ethanol containing three equivalents of HCl; the finished product is extracted as the HCl salt, m.p. 123-124°.<ref name = Hartung/>

			== Presence ==
			In 2015, 52% of supplements labeled as containing '']'' were found to contain BMPEA.<ref name=cohen2015>{{cite journal \| vauthors = Cohen PA, Bloszies C, Yee C, Gerona R \| title = An amphetamine isomer whose efficacy and safety in humans has never been studied, β-methylphenylethylamine (BMPEA), is found in multiple dietary supplements \| journal = Drug Testing and Analysis \| volume = 8 \| issue = 3–4 \| pages = 328–333 \| year = 2016 \| pmid = 25847603 \| doi = 10.1002/dta.1793 \| doi-access = free }}</ref><ref>{{cite news \| vauthors = ((The Editorial Board)) \|title=Conflicts of Interest at the F.D.A. \|url=https://www.nytimes.com/2015/04/13/opinion/conflicts-of-interest-at-the-fda.html \|quote= they identified BMPEA in 11 of 21 brands of supplements with acacia rigidula listed as an ingredient.\|newspaper=] \|date=April 13, 2015 \|access-date=2015-04-13 }}</ref> Consumers following recommended maximum daily servings would consume a maximum of 94 mg of BMPEA per day.<ref name=cohen2015/> In 2012, however, the FDA determined that BMPEA was not naturally present in ''Acacia rigidula'' leaves.<ref>{{cite web\|url=http://www.webmd.com/vitamins-and-supplements/news/20150407/bmpea-acacia-rigidula-supplments\|title=Untested Stimulant Still in Dietary Supplements\| vauthors = Goodman B \|website=WebMD\|date=7 April 2015}}</ref> This question was litigated during the trial of ''Hi Tech Pharmaceuticals Inc vs. Cohen''.<ref>{{cite journal \| vauthors = Bagley N, Carroll AE, Cohen PA \| title = Scientific Trials-In the Laboratories, Not the Courts \| journal = JAMA Internal Medicine \| volume = 178 \| issue = 1 \| pages = 7–8 \| date = January 2018 \| pmid = 29114742 \| doi = 10.1001/jamainternmed.2017.5730 \| url = http://nrs.harvard.edu/urn-3:HUL.InstRepos:34902783 }}</ref><ref>{{cite web\|title=BMPEA and Acacia Rigidula: Hi-Tech Pharmaceuticals Fights Back\|url=https://blog.priceplow.com/bmpea#natural\|website=PricePlow\|access-date=27 October 2015\|date=26 October 2015}}</ref> Despite US Food and Drug Administration warning letters, BMPEA remains present in dietary supplements.<ref>{{cite journal \| vauthors = Cohen PA, Wen A, Gerona R \| title = Prohibited Stimulants in Dietary Supplements After Enforcement Action by the US Food and Drug Administration \| journal = JAMA Internal Medicine \| volume = 178 \| issue = 12 \| pages = 1721–1723 \| date = December 2018 \| pmid = 30422217 \| pmc = 6583602 \| doi = 10.1001/jamainternmed.2018.4846 }}</ref>

			== Safety ==
			β-Methylphenethylamine was associated with a case of cerebral hemorrhage in a Swedish athlete and first time user. The female victim with no medical history had taken a Swedish ] with 290 mg β-methylphenethylamine per serving before commencing her usual exercises. After about 30 minutes the first symptoms appeared. The presence of the active ingredient was not declared on the label.<ref name = Cohen>{{cite journal \| vauthors = Cohen PA, Zeijlon R, Nardin R, Keizers PH, Venhuis B \| title = Hemorrhagic Stroke Probably Caused by Exercise Combined With a Sports Supplement Containing β-Methylphenyl-ethylamine (BMPEA): A Case Report \| journal = Annals of Internal Medicine \| volume = 162 \| issue = 12 \| pages = 879–880 \| date = June 2015 \| pmid = 26075771 \| doi = 10.7326/L15-5101 \| url = http://nrs.harvard.edu/urn-3:HUL.InstRepos:40997747 }}</ref> Use of β-Methylphenethylamine is also prohibited in sports.<ref name = Cholbinski>{{cite journal \| vauthors = Chołbiński P, Wicka M, Kowalczyk K, Jarek A, Kaliszewski P, Pokrywka A, Bulska E, Kwiatkowska D \| display-authors = 6 \| title = Detection of β-methylphenethylamine, a novel doping substance, by means of UPLC/MS/MS \| journal = Analytical and Bioanalytical Chemistry \| volume = 406 \| issue = 15 \| pages = 3681–3688 \| date = June 2014 \| pmid = 24633566 \| pmc = 4026626 \| doi = 10.1007/s00216-014-7728-5 }}</ref>

	== See also ==		== See also ==
	* ]		* ]
			* ]
	* ]		* ]
			* ] (''N''-methyl-β-methylphenethylamine)

	== References ==		== References ==
	{{Reflist\|2}}		{{Reflist}}

			{{Monoamine releasing agents}}
	{{Stimulants}}
	{{~~Adrenergics~~}}		{{TAAR ligands}}
	{{Dopaminergics}}
	{{Phenethylamines}}		{{Phenethylamines}}

	{{DEFAULTSORT:Methylphenethylamine, Beta-}}		{{DEFAULTSORT:Methylphenethylamine, Beta-}}

	]		]
	]		]
			]

			]

	{{nervous-system-drug-stub}}

Latest revision as of 05:17, 8 December 2024

Chemical compound

Pharmaceutical compound

β-Methylphenethylamine
Clinical data


ATC code	none
Legal status
Legal status	US: Unapproved "New Drug" (as defined by 21 U.S. Code § 321(p)(1)). Use in dietary supplements, food, or medicine is unlawful; otherwise uncontrolled.
Identifiers
IUPAC name 2-Phenylpropan-1-amine
CAS Number	582-22-9
PubChem CID	11398
ChemSpider	10920
UNII	6XL7O3V13L
ChEBI	CHEBI:229522
ChEMBL	ChEMBL158578
CompTox Dashboard (EPA)	DTXSID10870630
ECHA InfoCard	100.008.619
Chemical and physical data
Formula	C₉H₁₃N
Molar mass	135.210 g·mol
3D model (JSmol)	Interactive image
Density	0.93 g/cm
Boiling point	80 °C (176 °F) (at 10 mm Hg)
SMILES NCC(c1ccccc1)C
InChI InChI=1S/C9H13N/c1-8(7-10)9-5-3-2-4-6-9/h2-6,8H,7,10H2,1H3 Key:AXORVIZLPOGIRG-UHFFFAOYSA-N
(verify)

β-Methylphenethylamine (β-Me-PEA, BMPEA, or 1-amino-2-phenylpropane) is an organic compound of the phenethylamine class, and a positional isomer of the drug amphetamine, with which it shares some properties. In particular, both amphetamine and β-methylphenethylamine are human TAAR1 agonists. In appearance, it is a colorless or yellowish liquid.

Relatively little information has been published about this substance. Hartung and Munch reported that it had good antihypotensive (pressor) activity in experimental animals, and that it was orally active. The MLD (minimum lethal dose) for the HCl salt was given as 500 mg/kg (rat, s.c.) and 50 mg/kg (rabbit, i.v.).

A study by Graham and co-workers at the Upjohn Co., comparing many β-methylphenethylamines substituted on the benzene ring showed that β-methylphenethylamine itself had 1/700 x the pressor activity of epinephrine, corresponding to ~ 1/3 the potency of amphetamine. The β-methyl compound also had ~ 2 x the broncho-dilating power of amphetamine (as measured using the isolated rabbit lung), and an LD₅₀ of 50 mg/kg (rat, i.v.).

Synthesis

β-Methylphenethylamine can be made by the catalytic hydrogenation of 2-phenylpropionitrile with Pd/C in pure anhydrous ethanol containing three equivalents of HCl; the finished product is extracted as the HCl salt, m.p. 123-124°.

Presence

In 2015, 52% of supplements labeled as containing Acacia rigidula were found to contain BMPEA. Consumers following recommended maximum daily servings would consume a maximum of 94 mg of BMPEA per day. In 2012, however, the FDA determined that BMPEA was not naturally present in Acacia rigidula leaves. This question was litigated during the trial of Hi Tech Pharmaceuticals Inc vs. Cohen. Despite US Food and Drug Administration warning letters, BMPEA remains present in dietary supplements.

Safety

β-Methylphenethylamine was associated with a case of cerebral hemorrhage in a Swedish athlete and first time user. The female victim with no medical history had taken a Swedish food supplement with 290 mg β-methylphenethylamine per serving before commencing her usual exercises. After about 30 minutes the first symptoms appeared. The presence of the active ingredient was not declared on the label. Use of β-Methylphenethylamine is also prohibited in sports.

References

"BMPEA in Dietary Supplements". FDA. 22 February 2023. Retrieved 9 June 2023.
Wainscott DB, Little SP, Yin T, Tu Y, Rocco VP, He JX, Nelson DL (January 2007). "Pharmacologic characterization of the cloned human trace amine-associated receptor1 (TAAR1) and evidence for species differences with the rat TAAR1". The Journal of Pharmacology and Experimental Therapeutics. 320 (1): 475–485. doi:10.1124/jpet.106.112532. PMID 17038507. S2CID 10829497. The effect of β-carbon substitution on the phenylethylamine side chain was also investigated (Table 3). A β-methyl substituent was well tolerated compared with β-PEA. In fact, S-(–)-β-methyl-β-PEA was as potent as β-PEA at human TAAR1.
^ Hartung WH, Munch JC (1931). "Amino alcohols. VI. The preparation and pharmacodynamic activity of four isomeric phenylpropylamines". J. Am. Chem. Soc. 53 (5): 1875–9. doi:10.1021/ja01356a036.
Graham BE, Cartland GF, Woodruff EH (1945). "Phenyl propyl and phenyl isopropyl amines. Changes in pharmacological action on substitution of phenyl nucleus and amino nitrogen". Ind. Eng. Chem. 37 (2): 149–51. doi:10.1021/ie50422a010.
^ Cohen PA, Bloszies C, Yee C, Gerona R (2016). "An amphetamine isomer whose efficacy and safety in humans has never been studied, β-methylphenylethylamine (BMPEA), is found in multiple dietary supplements". Drug Testing and Analysis. 8 (3–4): 328–333. doi:10.1002/dta.1793. PMID 25847603.
The Editorial Board (13 April 2015). "Conflicts of Interest at the F.D.A." The New York Times. Retrieved 13 April 2015. they identified BMPEA in 11 of 21 brands of supplements with acacia rigidula listed as an ingredient.
Goodman B (7 April 2015). "Untested Stimulant Still in Dietary Supplements". WebMD.
Bagley N, Carroll AE, Cohen PA (January 2018). "Scientific Trials-In the Laboratories, Not the Courts". JAMA Internal Medicine. 178 (1): 7–8. doi:10.1001/jamainternmed.2017.5730. PMID 29114742.
"BMPEA and Acacia Rigidula: Hi-Tech Pharmaceuticals Fights Back". PricePlow. 26 October 2015. Retrieved 27 October 2015.
Cohen PA, Wen A, Gerona R (December 2018). "Prohibited Stimulants in Dietary Supplements After Enforcement Action by the US Food and Drug Administration". JAMA Internal Medicine. 178 (12): 1721–1723. doi:10.1001/jamainternmed.2018.4846. PMC 6583602. PMID 30422217.
Cohen PA, Zeijlon R, Nardin R, Keizers PH, Venhuis B (June 2015). "Hemorrhagic Stroke Probably Caused by Exercise Combined With a Sports Supplement Containing β-Methylphenyl-ethylamine (BMPEA): A Case Report". Annals of Internal Medicine. 162 (12): 879–880. doi:10.7326/L15-5101. PMID 26075771.
Chołbiński P, Wicka M, Kowalczyk K, Jarek A, Kaliszewski P, Pokrywka A, et al. (June 2014). "Detection of β-methylphenethylamine, a novel doping substance, by means of UPLC/MS/MS". Analytical and Bioanalytical Chemistry. 406 (15): 3681–3688. doi:10.1007/s00216-014-7728-5. PMC 4026626. PMID 24633566.

Monoamine releasing agents

DRAsTooltip Dopamine releasing agents

Morpholines: Fenbutrazate Fenmetramide Morazone Morforex Phendimetrazine Phenmetrazine Pseudophenmetrazine
Oxazolines: 4-MAR Aminorex Clominorex Cyclazodone Fenozolone Fluminorex Pemoline Thozalinone
Phenethylamines: 2-OH-PEA 4-CAB 4-FA 4-FMA 4-MA 4-MMA Alfetamine Amfecloral Amfepentorex Amfepramone Amphetamine (Dextroamphetamine Levoamphetamine) Amphetaminil β-Me-PEA BDB BOH Benzphetamine Buphedrone Butylone Cathine Cathinone Clobenzorex Clortermine D-Deprenyl DMA DMMA Dimethylamphetamine Ephedrine Ethcathinone EBDB Ethylone Etilamfetamine Famprofazone Fenethylline Fenproporex Flephedrone Fludorex Furfenorex Hordenine 4-Hydroxyamphetamine Iofetamine (123I) Lisdexamfetamine Lophophine Mefenorex Mephedrone Metamfepramone Methamphetamine Dextromethamphetamine Levomethamphetamine Methcathinone Methedrone MMDA MMDMA MBDB MDA (tenamfetamine) MDEA MDMA (midomafetamine) MDMPEA MDOH MDPEA Methylone Morforex Ortetamine pBA pCA pIA Pholedrine Phenethylamine Pholedrine Phenpromethamine Prenylamine Propylamphetamine Pseudoephedrine Tiflorex Tyramine Xylopropamine Zylofuramine
Piperazines: 2C-B-BZP BZP MBZP MDBZP MeOPP oMPP
Others: 2-ADN 2-AI 2-AT 4-BP 5-APDI 5-IAI Amineptine Clofenciclan Cyclopentamine Cypenamine Cyprodenate Feprosidnine Gilutensin Heptaminol Hexacyclonate Indanorex Isometheptene Methylhexanamine Naphthylaminopropane Octodrine Phthalimidopropiophenone Phenylbiguanide Propylhexedrine

NRAsTooltip Norepinephrine releasing agents

Morpholines: Fenbutrazate Fenmetramide Morazone Morforex Phendimetrazine Phenmetrazine Pseudophenmetrazine
Oxazolines: 4-MAR Aminorex Clominorex Cyclazodone Fenozolone Fluminorex Pemoline Thozalinone
Phenethylamines: 2-OH-PEA 4-CAB 4-FA 4-FMA 4-MA 4-MMA Alfetamine Amfecloral Amfepentorex Amfepramone Amphetamine Dextroamphetamine Levoamphetamine Amphetaminil β-Me-PEA BDB Benzphetamine BOH Buphedrone Butylone Cathine Cathinone Clobenzorex Clortermine Dimethylamphetamine DMA DMMA EBDB Ephedrine Ethcathinone Ethylone Etilamfetamine Famprofazone Fenethylline Fenproporex Flephedrone Fludorex Furfenorex Hordenine 4-Hydroxyamphetamine 5-APDI (IAP) Iofetamine (123I) Lisdexamfetamine Lophophine MBDB MDA (tenamfetamine) MDEA MDMA (midomafetamine) Metamfepramone MDMPEA MDOH MDPEA Mefenorex Mephedrone Mephentermine Methamphetamine Dextromethamphetamine Levomethamphetamine Methcathinone Methedrone Methylone Morforex Naphthylaminopropane Ortetamine pBA pCA Pentorex Phenethylamine Pholedrine Phenpromethamine Phentermine Phenylpropanolamine pIA Prenylamine Propylamphetamine Pseudoephedrine Selegiline (also D-Deprenyl) Tiflorex Tyramine Xylopropamine Zylofuramine
Piperazines: 2C-B-BZP BZP MBZP mCPP MDBZP MeOPP oMPP pFPP
Others: 2-ADN 2-AI 2-AT 2-BP 4-BP 5-IAI Clofenciclan Cyclopentamine Cypenamine Cyprodenate Feprosidnine Gilutensin Heptaminol Hexacyclonate Indanorex Isometheptene Methylhexanamine Octodrine Phthalimidopropiophenone Propylhexedrine Tuaminoheptane

SRAsTooltip Serotonin releasing agents

Aminoindanes: 5-IAI AMMI ETAI MDAI MDMAI MMAI TAI
Aminotetralins: 6-CAT 8-OH-DPAT MDAT MDMAT
Oxazolines: 4-Methylaminorex Aminorex Clominorex Fluminorex
Phenethylamines: 2-Methyl-MDA 4-CAB 4-FA 4-FMA 4-HA 4-MTA 5-APDB 5-Methyl-MDA 6-APDB 6-Methyl-MDA AEMMA Amiflamine BDB BOH Brephedrone Butylone Chlorphentermine Cloforex Amfepramone Metamfepramone DCA Dexfenfluramine DFMDA DMA DMMA EBDB EDMA Ethylone Etolorex Fenfluramine Flephedrone Flucetorex IAP Iofetamine Levofenfluramine Lophophine MBDB MDA (tenamfetamine) MDEA MDHMA MDMA (midomafetamine) MDMPEA MDOH MDPEA Mephedrone Methedrone Methylone MMA MMDA MMDMA MMMA NAP Norfenfluramine 4-TFMA pBA pCA pIA PMA PMEA PMMA TAP
Piperazines: 2C-B-BZP 3-MeOPP BZP DCPP MBZP mCPP MDBZP MeOPP Mepiprazole oMPP pCPP pFPP pTFMPP TFMPP
Tryptamines: 4-Methyl-αET 4-Methyl-αMT 5-CT 5-MeO-αET 5-MeO-αMT 5-MT αET αMT DMT Tryptamine
Others: Indeloxazine Viqualine

Others

DAT modulators: Agonist-like: SoRI-9804
SoRI-20040; Antagonist-like: SoRI-20041

Adrenergic release blockers: Bethanidine
Bretylium
Guanadrel
Guanazodine
Guanethidine
Guanoxan

See also: Receptor/signaling modulators • Monoamine reuptake inhibitors • Adrenergics • Dopaminergics • Serotonergics • Monoamine metabolism modulators • Monoamine neurotoxins

Trace amine-associated receptor modulators

TAAR1Tooltip Trace amine-associated receptor 1

EPPTB (RO-5212773)

TAAR5Tooltip Trace amine-associated receptor 5

Agonists	N,N-Dimethylethylamine Trimethylamine
Inverse agonists	3-Iodothyronamine

Notes: (1) TAAR1 activity of ligands varies significantly between species. Some agents that are TAAR1 ligands in some species are not in other species. This navbox includes all TAAR1 ligands regardless of species. (2) See the individual pages for references, as well as the List of trace amines, TAAR, and TAAR1 pages. See also: Receptor/signaling modulators

v t e Phenethylamines
Phenethylamines	Psychedelics: 25B-NBOMe 25C-NBOMe 25D-NBOMe 25I-NBOMe 25N-NBOMe 2C-B 2C-B-AN 2C-Bn 2C-Bu 2C-C 2C-CN 2C-CP 2C-D 2C-E 2C-EF 2C-F 2C-G 2C-G-1 2C-G-2 2C-G-3 2C-G-4 2C-G-5 2C-G-6 2C-G-N 2C-H 2C-I 2C-iP 2C-N 2C-NH2 2C-O 2C-O-4 2C-P 2C-Ph 2C-SE 2C-T 2C-T-2 2C-T-3 2C-T-4 2C-T-5 2C-T-6 2C-T-7 2C-T-8 2C-T-9 2C-T-10 2C-T-11 2C-T-12 2C-T-13 2C-T-14 2C-T-15 2C-T-16 2C-T-17 2C-T-18 2C-T-19 2C-T-20 2C-T-21 2C-T-22 2C-T-22.5 2C-T-23 2C-T-24 2C-T-25 2C-T-27 2C-T-28 2C-T-30 2C-T-31 2C-T-32 2C-T-33 2C-TFE 2C-TFM 2C-YN 2C-V Allylescaline DESOXY Escaline Isoproscaline Jimscaline Macromerine MEPEA Mescaline Metaescaline Methallylescaline Proscaline Psi-2C-T-4 TCB-2 Stimulants: Phenylethanolamine Hordenine Phenethylamine Phenpromethamine α-Methylphenethylamine (amphetamine) β-Methylphenethylamine m-Methylphenethylamine N-Methylphenethylamine o-Methylphenethylamine p-Methylphenethylamine Methylphenidate Entactogens: Lophophine MDPEA MDMPEA Others: BOH DMPEA
Amphetamines	Psychedelics: 3C-AL 3C-BZ 3C-E 3C-MAL 3C-P Aleph Beatrice Bromo-DragonFLY D-Deprenyl DMA DMCPA DMMDA DOB DOC DOEF DOET DOI DOM DON DOPR DOTFM Ganesha MMDA MMDA-2 Psi-DOM TMA TeMA ZDCM-04 Stimulants: 2-FA 2-FMA 3-FA 3-FMA Acridorex Alfetamine Amfecloral Amfepentorex Amphetamine (Dextroamphetamine, Levoamphetamine) Amphetaminil Benfluorex Benzphetamine Cathine Clobenzorex Dimethylamphetamine Ephedrine Etilamfetamine Fencamfamin Fencamine Fenethylline Fenfluramine (Dexfenfluramine, Levofenfluramine) Fenproporex Flucetorex Fludorex Formetorex Furfenorex Gepefrine 4-Hydroxyamphetamine Iofetamine Isopropylamphetamine Lefetamine Lisdexamfetamine Mefenorex Metaraminol Methamphetamine (Dextromethamphetamine, Levomethamphetamine) Methoxyphenamine MMA Morforex Norfenfluramine L-Norpseudoephedrine N,alpha-Diethylphenylethylamine Oxifentorex Oxilofrine Ortetamine PBA PCA PFA PFMA PIA PMA PMEA PMMA Phenylpropanolamine Pholedrine Prenylamine Propylamphetamine Pseudoephedrine Sibutramine Tiflorex Tranylcypromine Xylopropamine Zylofuramine Entactogens: 4-FA 4-FMA 4-MA 4-MMA 4-MTA 5-APB 5-APDB 5-EAPB 5-IT 5-MAPB 5-MAPDB 6-APB 6-APDB 6-Chloro-MDMA 6-EAPB 6-IT 6-MAPB 6-MAPDB EDA IAP 2,3-MDA 3,4-MDA (tenamfetamine) MDEA MDHMA MDMA (midomafetamine) MDOH Methamnetamine MMDMA Naphthylaminopropane TAP Others: 3,4-DCA Amiflamine DiFMDA Selegiline (also D-Deprenyl)
Phentermines	Stimulants: Chlorphentermine Cloforex Clortermine Etolorex Mephentermine Pentorex Phentermine Entactogens: MDPH MDMPH Others: Cericlamine
Cathinones	Stimulants: 3-FMC 4-MC 4-BMC 4-CMC 4-EMC 4-FMC 4-MEC 4-MeMABP 4-MPD Amfepramone Benzedrone Brephedrone Buphedrone Bupropion Cathinone Dimethylcathinone Ethcathinone Eutylone Hydroxybupropion Methcathinone Methedrone NEB N-Ethylhexedrone N-Ethylpentedrone Pentedrone Pentylone Radafaxine Entactogens: 3,4-DMMC 3-MMC Butylone Ethylone Methylone Methylenedioxycathinone Mephedrone
Phenylisobutylamines	Entactogens: 4-CAB 4-MAB Ariadne BDB Butylone EBDB Eutylone MBDB Stimulants: Phenylisobutylamine
Phenylalkylpyrrolidines	Stimulants: α-PBP α-PHP α-PPP α-PVP MDPBP MDPPP MDPV 4-MePBP 4-MePHP 4-MePPP MOPPP MOPVP MPBP MPHP MPPP Naphyrone PEP Prolintane Pyrovalerone
Catecholamines (and close relatives)	6-FNE 6-OHDA a-Me-DA a-Me-TRA Adrenochrome Ciladopa D-DOPA (Dextrodopa) Dimetofrine Dopamine Epinephrine Epinine Etilefrine Ethylnorepinephrine Fenclonine Ibopamine Isoprenaline Isoetarine L-DOPA (Levodopa) L-DOPS (Droxidopa) L-Phenylalanine L-Tyrosine m-Tyramine Metanephrine Metaraminol Metaterol Metirosine Methyldopa N,N-Dimethyldopamine Nordefrin (Levonordefrin) Norepinephrine Norfenefrine (m-Octopamine) Normetanephrine Orciprenaline p-Octopamine p-Tyramine Phenylephrine Synephrine
Miscellaneous	AL-LAD Amidephrine Arbutamine Cafedrine Denopamine Desvenlafaxine Diphenidine Dizocilpine Dobutamine Dopexamine Ephenidine Etafedrine ETH-LAD Famprofazone Fluorolintane Hexapradol IP-LAD Lysergic acid amide Lysergic acid 2-butyl amide Lysergic acid 2,4-dimethylazetidide Lysergic acid diethylamide Methoxamine Methoxphenidine MT-45 PARGY-LAD Phenibut PRO-LAD Pronethalol Salbutamol (Levosalbutamol) Solriamfetol Theodrenaline Thiamphenicol UWA-101 Venlafaxine

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