7-PET

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-methanobenzofuro[3,2-e]isoquinolin-14-yl)-4-phenylbutan-2-ol;
CAS Number	13965-63-4 ;
PubChem CID	203125;
ChemSpider	21106246 ;
UNII	EA1GYF2V3I;
CompTox Dashboard (EPA)	DTXSID30912329 ;
Chemical and physical data
Formula	C31H39NO4
Molar mass	489.656 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O[C@](C)(CCc1ccccc1)[C@H]7CC64\C=C/[C@@]7(OC)[C@@H]5Oc2c3c(ccc2OC)C[C@H]6N(CC[C@@]345)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 ;
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7-PET is an opioid analgesic drug that has 300 times the potency of morphine by weight.^[1] It was discovered by K.W. Bentley^[2] 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,^[3]^[4] and unexpectedly the 3-hydrogen compound is also around the same potency of 2000 times morphine.^[5]

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.

References

^ 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.
^ 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.
^ 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.
^ 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.
^ 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.

[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.

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See also

References