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{{Short description|Opioid analgesic drug}}
{{Drugbox {{Drugbox
| Verifiedfields = changed
⚫ | verifiedrevid = 447991324
| Watchedfields = changed
| IUPAC_name = 7-endoethenotetrahydrothebaine
⚫ | verifiedrevid = 477226838
⚫ | image = 7-PET_structure.png
| IUPAC_name = (2''R'')-2-((4''R'',7''S'',7a''R'',12b''S'',14''R'')-7,9-dimethoxy-3-methyl-1,2,3,4,7,7a-hexahydro-7,4a-ethano-4,12-methanobenzofuroisoquinolin-14-yl)-4-phenylbutan-2-ol
⚫ | image = 7-PET.svg
| width = 150px


<!--Clinical data--> <!--Clinical data-->
| tradename = | tradename =
| legal_status = | legal_status =


<!--Identifiers--> <!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|??}} | CAS_number_Ref = {{cascite|changed|??}}
| CAS_number = 13965-63-4 | CAS_number = 13965-63-4
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = EA1GYF2V3I
| PubChem = 203125 | PubChem = 203125
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
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<!--Chemical data--> <!--Chemical data-->
| C=31 | H=39 | N=1 | O=4 | C=31 | H=39 | N=1 | O=4
| smiles = O(C)(CCc1ccccc1)7CC64\C=C/7(OC)5Oc2c3c(ccc2OC)C6N(CC345)C
| molecular_weight = 487.64 g/mol
| smiles = CN5CCC16c4c2OC1C3(OC)C=CC6(C5Cc4ccc2OC)CC3C(O)(C)CCc7ccccc7
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C31H39NO4/c1-28(33,13-12-20-8-6-5-7-9-20)23-19-29-14-15-31(23,35-4)27-30(29)16-17-32(2)24(29)18-21-10-11-22(34-3)26(36-27)25(21)30/h5-11,23-24,27,33H,12-19H2,1-4H3/t23?,24-,27?,28?,29-,30+,31-/m1/s1 | StdInChI = 1S/C31H39NO4/c1-28(33,13-12-20-8-6-5-7-9-20)23-19-29-14-15-31(23,35-4)27-30(29)16-17-32(2)24(29)18-21-10-11-22(34-3)26(36-27)25(21)30/h5-11,23-24,27,33H,12-19H2,1-4H3/t23?,24-,27?,28?,29-,30+,31-/m1/s1
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}} }}


'''7-PET''' was discovered by K.W. Bentley<ref>Bentley,K.W. et al. Journal of the American Chemical Society, 1967, vol. 89, p. 3273 - 3280</ref> and is a potent ] drug, 300 times the potency of ] by weight.<ref>Lewis JW, Bentley KW, Cowan A. Narcotic Analgesics and Antagonists. ''Annual Reviews in Pharmacology'' 1971;11:241-270.</ref> It is related to the more well-known ] derivative opioid ], which is used as a very potent ] painkiller and ] medication, used primarily for the sedation of large animals such as elephants, giraffes and rhinos. 7-PET itself has a 3-O-methyl ether which reduces potency, but the 3-OH derivative is around 2200x morphine, almost the same potency as etorphine as a ] ],<ref>Feinberg AP, Creese I, Snyder SH. The opiate receptor: a model explaining structure-activity relationships of opiate agonists and antagonists. ''Proceedings of the National Academy of Sciences U S A''. 1976 Nov;73(11):4215-9.</ref><ref>Bentley KW, Lewis JW. Agonist and Antagonist Actions of Narcotic Analgesic Drugs. pp 7-16. University Park Press, Baltimore. (1973)</ref> and unexpectedly the 3-desoxy compound is also around the same potency of 2000x morphine.<ref>{{Cite doi|10.1021/jm00297a041}}</ref> '''7-PET''' is an ] ] drug that has 300 times the potency of ] by weight.<ref>{{cite journal | vauthors = Lewis JW, Bentley KW, Cowan A | title = Narcotic analgesics and antagonists | journal = Annual Review of Pharmacology | volume = 11 | pages = 241–270 | year = 1971 | pmid = 4948499 | doi = 10.1146/annurev.pa.11.040171.001325 }}</ref> It was discovered by K.W. Bentley<ref>{{cite journal | vauthors = Bentley KW, Hardy DG, Meek B | title = Novel analgesics and molecular rearrangements in the morphine-thebaine group. II. Alcohols derived from 6,14-endo-etheno- and 6,14-endo-ethanotetrahydrothebaine | journal = Journal of the American Chemical Society | volume = 89 | issue = 13 | pages = 3273–3280 | date = June 1967 | pmid = 6042763 | doi = 10.1021/ja00989a031 }}</ref> and is related to the more well known ] derivative ], which is used as a ] painkiller and ] medication for the sedation of large animals such as elephants, giraffes, and rhinos. 7-PET itself has a 3-''O''-methyl ether which reduces potency, but the 3-OH derivative is around 2200 times more potent than morphine, almost the same potency as etorphine as a ] ],<ref>{{cite journal | vauthors = Feinberg AP, Creese I, Snyder SH | title = The opiate receptor: a model explaining structure-activity relationships of opiate agonists and antagonists | journal = Proceedings of the National Academy of Sciences of the United States of America | volume = 73 | issue = 11 | pages = 4215–4219 | date = November 1976 | pmid = 186791 | pmc = 431391 | doi = 10.1073/pnas.73.11.4215 | doi-access = free | bibcode = 1976PNAS...73.4215F }}</ref><ref>{{ cite book | vauthors = Bentley KW, Lewis JW | veditors = Kosterlitz HW, Collier HO, Villarreal JE | title = Agonist and Antagonist Actions of Narcotic Analgesic Drugs | pages = 7–16 | publisher = University Park Press | location = Baltimore | year = 1973 | isbn = 978-0839107255 | lccn = 72012612 }}</ref> and unexpectedly the 3-hydrogen compound is also around the same potency of 2000 times morphine.<ref>{{cite journal | vauthors = Lewis JW, Readhead MJ | title = Novel analgetics and molecular rearrangements in the morphine-thebaine group. 18. 3-deoxy-6,14-endo-etheno-6,7,8,14-tetrahydrooripavines | journal = Journal of Medicinal Chemistry | volume = 13 | issue = 3 | pages = 525–527 | date = May 1970 | pmid = 5441135 | doi = 10.1021/jm00297a041 }}</ref>


Unlike etorphine however, 7-PET is not an illegal drug, and is not controlled under the UN drug conventions, but it might still be considered to be a ] of etorphine on the grounds of its related chemical structure in some jurisdictions such as the ], ], ] and ]. Unlike etorphine, 7-PET is not controlled under the UN drug conventions, but it might still be considered to be a ] of etorphine on the grounds of its related chemical structure in some jurisdictions such as the United States, Canada, Australia, and New Zealand.


⚫ == See also ==

{{analgesic-stub}}

⚫ ==See also==
* ] * ]
* ] * ]
* ] * ]
* ]
* ] * ]
* ] * ]
* ] * ]
* ] * ]


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

{{Opioidergics}}


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Latest revision as of 13:35, 29 December 2023

Opioid analgesic drug Pharmaceutical compound
7-PET
Identifiers
IUPAC name
  • (2R)-2-((4R,7S,7aR,12bS,14R)-7,9-dimethoxy-3-methyl-1,2,3,4,7,7a-hexahydro-7,4a-ethano-4,12-methanobenzofuroisoquinolin-14-yl)-4-phenylbutan-2-ol
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC31H39NO4
Molar mass489.656 g·mol
3D model (JSmol)
SMILES
  • O(C)(CCc1ccccc1)7CC64\C=C/7(OC)5Oc2c3c(ccc2OC)C6N(CC345)C
InChI
  • InChI=1S/C31H39NO4/c1-28(33,13-12-20-8-6-5-7-9-20)23-19-29-14-15-31(23,35-4)27-30(29)16-17-32(2)24(29)18-21-10-11-22(34-3)26(36-27)25(21)30/h5-11,23-24,27,33H,12-19H2,1-4H3/t23?,24-,27?,28?,29-,30+,31-/m1/s1
  • Key:CSZMZMPPNJFGRW-TZBHJBKBSA-N
  (what is this?)  (verify)

7-PET is an opioid analgesic drug that has 300 times the potency of morphine by weight. It was discovered by K.W. Bentley and is related to the more well known oripavine derivative etorphine, which is used as a veterinary painkiller and anesthetic medication for the sedation of large animals such as elephants, giraffes, and rhinos. 7-PET itself has a 3-O-methyl ether which reduces potency, but the 3-OH derivative is around 2200 times more potent than morphine, almost the same potency as etorphine as a μ agonist, and unexpectedly the 3-hydrogen compound is also around the same potency of 2000 times morphine.

Unlike etorphine, 7-PET is not controlled under the UN drug conventions, but it might still be considered to be a controlled substance analogue of etorphine on the grounds of its related chemical structure in some jurisdictions such as the United States, Canada, Australia, and New Zealand.

See also

References

  1. Lewis JW, Bentley KW, Cowan A (1971). "Narcotic analgesics and antagonists". Annual Review of Pharmacology. 11: 241–270. doi:10.1146/annurev.pa.11.040171.001325. PMID 4948499.
  2. Bentley KW, Hardy DG, Meek B (June 1967). "Novel analgesics and molecular rearrangements in the morphine-thebaine group. II. Alcohols derived from 6,14-endo-etheno- and 6,14-endo-ethanotetrahydrothebaine". Journal of the American Chemical Society. 89 (13): 3273–3280. doi:10.1021/ja00989a031. PMID 6042763.
  3. Feinberg AP, Creese I, Snyder SH (November 1976). "The opiate receptor: a model explaining structure-activity relationships of opiate agonists and antagonists". Proceedings of the National Academy of Sciences of the United States of America. 73 (11): 4215–4219. Bibcode:1976PNAS...73.4215F. doi:10.1073/pnas.73.11.4215. PMC 431391. PMID 186791.
  4. Bentley KW, Lewis JW (1973). Kosterlitz HW, Collier HO, Villarreal JE (eds.). Agonist and Antagonist Actions of Narcotic Analgesic Drugs. Baltimore: University Park Press. pp. 7–16. ISBN 978-0839107255. LCCN 72012612.
  5. Lewis JW, Readhead MJ (May 1970). "Novel analgetics and molecular rearrangements in the morphine-thebaine group. 18. 3-deoxy-6,14-endo-etheno-6,7,8,14-tetrahydrooripavines". Journal of Medicinal Chemistry. 13 (3): 525–527. doi:10.1021/jm00297a041. PMID 5441135.
Opioid receptor modulators
μ-opioid
(MOR)
Agonists
(abridged;
full list)
Antagonists
δ-opioid
(DOR)
Agonists
Antagonists
κ-opioid
(KOR)
Agonists
Antagonists
Nociceptin
(NOP)
Agonists
Antagonists
Others
  • Others: Kyotorphin (met-enkephalin releaser/degradation stabilizer)
Categories: