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
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC31H39NO4
Molar mass489.656 g·mol−1
3D model (JSmol)
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 checkY
  • Key:CSZMZMPPNJFGRW-TZBHJBKBSA-N checkY
 ☒NcheckY (what is this?)  (verify)

7-PET was discovered by K.W. Bentley[1] and is a potent opioid analgesic drug, 300 times the potency of morphine by weight.[2] It is related to the more well-known oripavine derivative opioid etorphine, which is used as a very potent veterinary painkiller and anesthetic 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 μ agonist,[3][4] and unexpectedly the 3-desoxy compound is also around the same potency of 2000x morphine.[5]

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 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. ↑ 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): 3273–80. doi:10.1021/ja00989a031. PMID 6042763.
  2. ↑ Lewis JW, Bentley KW, Cowan A (1971). "Narcotic analgesics and antagonists". Annual Review of Pharmacology. 11: 241–70. doi:10.1146/annurev.pa.11.040171.001325. PMID 4948499.
  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): 4215–9. Bibcode:1976PNAS...73.4215F. doi:10.1073/pnas.73.11.4215. PMC 431391. PMID 186791.
  4. ↑ Bentley, K. W.; Lewis, J. W. (1973). Kosterlitz, H. W.; Collier, H. O. J.; Villarreal, J. E. (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): 525–7. doi:10.1021/jm00297a041. PMID 5441135.
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