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{{Short description|Chemical compound}}
{{cs1 config|name-list-style=vanc}}
{{Drugbox {{Drugbox
| Verifiedfields = changed
| verifiedrevid = 443666762 | verifiedrevid = 447993914
| IUPAC_name = ethyl 1-- 4-phenylpiperidine- 4-carboxylate | IUPAC_name = ethyl 1-- 4-phenylpiperidine- 4-carboxylate
| image = Benzethidine.svg | image = Benzethidine.svg
| image_class = skin-invert-image
| width = 160 | width = 160
| alt = Structural formula of benzethidine

| image2 = Benzethidine 3D ball.png
| alt2 = Ball-and-stick model of the benzethidine molecule
| width2 = 260
<!--Clinical data--> <!--Clinical data-->
| tradename = | tradename =
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| pregnancy_US = <!-- A / B / C / D / X --> | pregnancy_US = <!-- A / B / C / D / X -->
| pregnancy_category = | pregnancy_category =
| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 --> | legal_AU = S9
| legal_BR = A1
| legal_BR_comment = <ref>{{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2023-03-31 |title=RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |url-status=live |archive-url=https://web.archive.org/web/20230803143925/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |archive-date=2023-08-03 |access-date=2023-08-16 |publisher=] |language=pt-BR |publication-date=2023-04-04}}</ref>
| legal_CA = Schedule I | legal_CA = Schedule I
| legal_UK = Class A | legal_UK = Class A
| legal_US = Schedule I | legal_US = Schedule I
| legal_DE = Anlage I
| legal_status = | legal_status =

<!--Pharmacokinetic data--> <!--Pharmacokinetic data-->
| bioavailability = | bioavailability =
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| elimination_half-life = | elimination_half-life =
| excretion = | excretion =

<!--Identifiers--> <!--Identifiers-->
| CASNo_Ref = {{cascite|??|??}} | CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 3691-78-9 | CAS_number = 3691-78-9
| ATC_prefix = none | ATC_prefix = none
| ATC_suffix = | ATC_suffix =
| PubChem = 62516 | PubChem = 62516
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 2104234
| DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB01518 | DrugBank = DB01518
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| UNII_Ref = {{fdacite|correct|FDA}} | UNII_Ref = {{fdacite|correct|FDA}}
| UNII = X0I74BAR02 | UNII = X0I74BAR02
| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = D12685
<!--Chemical data--> <!--Chemical data-->
| C=23 | H=29 | N=1 | O=3 | C=23 | H=29
| N=1 | O=3
| molecular_weight = 367.481 g/mol
| smiles = O=C(OCC)C3(c1ccccc1)CCN(CCOCc2ccccc2)CC3 | smiles = O=C(OCC)C3(c1ccccc1)CCN(CCOCc2ccccc2)CC3
| InChI = 1/C23H29NO3/c1-2-27-22(25)23(21-11-7-4-8-12-21)13-15-24(16-14-23)17-18-26-19-20-9-5-3-6-10-20/h3-12H,2,13-19H2,1H3
| InChIKey = UVTBZAWTRVBTMK-UHFFFAOYAQ
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C23H29NO3/c1-2-27-22(25)23(21-11-7-4-8-12-21)13-15-24(16-14-23)17-18-26-19-20-9-5-3-6-10-20/h3-12H,2,13-19H2,1H3 | StdInChI = 1S/C23H29NO3/c1-2-27-22(25)23(21-11-7-4-8-12-21)13-15-24(16-14-23)17-18-26-19-20-9-5-3-6-10-20/h3-12H,2,13-19H2,1H3
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}} }}


'''Benzethidine''' is a 4-]] derivative that is related to the ] ] drug ] (''meperidine'', or ''Demerol'').<ref>Maul C, Buschmann H, Sundermann B. Opioids: 3.3 Synthetic Opioids. ''Analgesics'' 2005; 159-169. ISBN 9783527304035</ref> '''Benzethidine''' is a 4-]] derivative that is related to the clinically used ] ] drug ] (''meperidine'', or ''Demerol'').<ref>{{cite book | vauthors = Maul C, Buschmann H, Sundermann B | chapter = Opioids: 3.3 Synthetic Opioids. | title = Analgesics | date = 2005 | pages = 159–169 | publisher = Wiley-VCH | isbn = 978-3-527-30403-5 }}</ref>


Benzethidine is not currently used in medicine and is a ]/] drug which is controlled under UN drug conventions. It has similar effects to other opioid derivatives, such as ], ], ] and ].<ref>Cahal DA, Dare JG, Keith D. A Sequential Trial of Analgesics in Labour. ''International Journal of Obstetrics and Gynaecology'' 1961; 68(1): 88–93.</ref> Benzethidine is not currently used in medicine and is a ]/] drug which is controlled under UN drug conventions. It has similar effects to other opioid derivatives, such as ], ], ] and ].<ref name="pmid13689779">{{cite journal | vauthors = Cahal DA, Dare JG, Keith D | title = A sequential trial of analgesics in labour | journal = The Journal of Obstetrics and Gynaecology of the British Commonwealth | volume = 68 | pages = 88–93 | date = February 1961 | pmid = 13689779 | doi = 10.1111/j.1471-0528.1961.tb02689.x | s2cid = 27397119 }}</ref> In the United States, the drug is a ] with a DEA ACSCN of 9606 and 2014 annual aggregate manufacturing quota of nil.<ref>{{Cite web | url=http://deadiversion.usdoj.gov/quotas/conv_factor/index.html |title = Conversion Factors for Controlled Substances | work = Diversion Control Division | publisher = Drug Enforcement Agency, U.S. Department of Justice }}</ref> The most common salt in use is the hydrochloride, free base conversion ratio of 0.910.

==Legal Status==

===Australia===
Benzethidine is considered a Schedule 9 prohibited substance in Australia under the ] (February 2017).<ref name="Poisons Standard">{{cite web | title = Poisons Standard | date = October 2015 | url = https://www.legislation.gov.au/Details/F2017L00057 | publisher = Australian Government }}</ref> A Schedule 9 substance is a substance which may be abused or misused, the manufacture, possession, sale or use of which should be prohibited by law except when required for medical or scientific research, or for analytical, teaching or training purposes with approval of Commonwealth and/or State or Territory Health Authorities.<ref name="Poisons Standard" />


== References == == References ==
{{Reflist|2}}
<references/>

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== External links ==
⚫ *


{{Opioidergics}}


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⚫ {{analgesic-stub}}


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Latest revision as of 21:36, 10 January 2025

Chemical compound

Pharmaceutical compound
Benzethidine
Structural formula of benzethidine
Ball-and-stick model of the benzethidine molecule
Clinical data
ATC code
  • none
Legal status
Legal status
Identifiers
IUPAC name
  • ethyl 1-- 4-phenylpiperidine- 4-carboxylate
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC23H29NO3
Molar mass367.489 g·mol
3D model (JSmol)
SMILES
  • O=C(OCC)C3(c1ccccc1)CCN(CCOCc2ccccc2)CC3
InChI
  • InChI=1S/C23H29NO3/c1-2-27-22(25)23(21-11-7-4-8-12-21)13-15-24(16-14-23)17-18-26-19-20-9-5-3-6-10-20/h3-12H,2,13-19H2,1H3
  • Key:UVTBZAWTRVBTMK-UHFFFAOYSA-N
  (what is this?)  (verify)

Benzethidine is a 4-phenylpiperidine derivative that is related to the clinically used opioid analgesic drug pethidine (meperidine, or Demerol).

Benzethidine is not currently used in medicine and is a Class A/Schedule I drug which is controlled under UN drug conventions. It has similar effects to other opioid derivatives, such as analgesia, sedation, nausea and respiratory depression. In the United States, the drug is a Schedule I Narcotic Controlled Substance with a DEA ACSCN of 9606 and 2014 annual aggregate manufacturing quota of nil. The most common salt in use is the hydrochloride, free base conversion ratio of 0.910.

Legal Status

Australia

Benzethidine is considered a Schedule 9 prohibited substance in Australia under the Poisons Standard (February 2017). A Schedule 9 substance is a substance which may be abused or misused, the manufacture, possession, sale or use of which should be prohibited by law except when required for medical or scientific research, or for analytical, teaching or training purposes with approval of Commonwealth and/or State or Territory Health Authorities.

References

  1. Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
  2. Maul C, Buschmann H, Sundermann B (2005). "Opioids: 3.3 Synthetic Opioids.". Analgesics. Wiley-VCH. pp. 159–169. ISBN 978-3-527-30403-5.
  3. Cahal DA, Dare JG, Keith D (February 1961). "A sequential trial of analgesics in labour". The Journal of Obstetrics and Gynaecology of the British Commonwealth. 68: 88–93. doi:10.1111/j.1471-0528.1961.tb02689.x. PMID 13689779. S2CID 27397119.
  4. "Conversion Factors for Controlled Substances". Diversion Control Division. Drug Enforcement Agency, U.S. Department of Justice.
  5. ^ "Poisons Standard". Australian Government. October 2015.

External links


Opioid receptor modulators
μ-opioid
(MOR)
Agonists
(abridged;
full list)
Antagonists
δ-opioid
(DOR)
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Antagonists
κ-opioid
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Nociceptin
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Others
  • Others: Kyotorphin (met-enkephalin releaser/degradation stabilizer)


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