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7-PET

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Revision as of 00:13, 19 November 2011 by CheMoBot (talk | contribs) (Updating {{drugbox}} (no changed fields - added verified revid - updated 'DrugBank_Ref', 'UNII_Ref', 'ChEMBL_Ref', 'ChEBI_Ref', 'KEGG_Ref', 'CAS_number_Ref') per Chem/Drugbox validation (report [[Misplaced Pages talk:WikiProject_Pharmac...)(diff) ← Previous revision | Latest revision (diff) | Newer revision → (diff) Pharmaceutical compound
7-PET
File:7-PET structure.png
Identifiers
IUPAC name
  • 7-endoethenotetrahydrothebaine
CAS Number
PubChem CID
ChemSpider
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC31H39NO4
Molar mass487.64 g/mol g·mol
3D model (JSmol)
SMILES
  • CN5CCC16c4c2OC1C3(OC)C=CC6(C5Cc4ccc2OC)CC3C(O)(C)CCc7ccccc7
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
  (verify)

7-PET was discovered by K.W. Bentley and is a potent analgesic drug, 300 times the potency of morphine by weight. 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, and unexpectedly the 3-desoxy compound is also around the same potency of 2000x morphine.

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 USA, Canada, Australia and New Zealand.


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See also

References

  1. Bentley,K.W. et al. Journal of the American Chemical Society, 1967, vol. 89, p. 3273 - 3280
  2. Lewis JW, Bentley KW, Cowan A. Narcotic Analgesics and Antagonists. Annual Reviews in Pharmacology 1971;11:241-270.
  3. 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.
  4. Bentley KW, Lewis JW. Agonist and Antagonist Actions of Narcotic Analgesic Drugs. pp 7-16. University Park Press, Baltimore. (1973)
  5. Attention: This template ({{cite doi}}) is deprecated. To cite the publication identified by doi:10.1021/jm00297a041, please use {{cite journal}} (if it was published in a bona fide academic journal, otherwise {{cite report}} with |doi=10.1021/jm00297a041 instead.
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