CP-47,497

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Structural formula
Structural formula of CP-47,497
General
Surname CP-47,497
other names

( Z ) -3- [4- (1,1-Dimethylheptyl) -2-hydroxyphenyl] cyclohexanol

Molecular formula C 21 H 34 O 2
External identifiers / databases
CAS number 70434-82-1
PubChem 125835
ChemSpider 10205286
Wikidata Q411899
Drug information
Drug class

Cannabinoid mimetic

Mechanism of action

Cannabinoid receptor CB 1 - agonist

properties
Molar mass 318.49 g · mol -1
Physical state

firmly

Melting point

109-110 ° C

safety instructions
GHS hazard labeling
no classification available
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

CP 47,497 is a cannabinoid receptor CB 1 - agonist , which in the 1980s by the company Pfizer has been developed. The substance has analgesic effects. CP-47,497 is highly biologically active and has a dissociation constant of 2.1 nmoles.

Descendants

CP-47,497 has three analogues that are also regulated by narcotics law in Germany.

Short name Surname IUPAC name
CP-47,497 ( cis -3- [4- (1,1-Dimethylheptyl) -2-hydroxyphenyl] -cyclohexanol) 5- (1,1-Dimethylheptyl) -2 - [(1 RS , 3 SR ) -3-hydroxycyclohexyl] phenol
CP-47,497-C6 homolog ( cis -3- [4- (1,1-Dimethylhexyl) -2-hydroxyphenyl] -cyclohexanol) 5- (1,1-Dimethylhexyl) -2 - [(1 RS , 3 SR ) -3-hydroxycyclohexyl] phenol
CP-47,497-C8 homolog or cannabicyclohexanol ( cis -3- [4- (1,1-Dimethyloctyl) -2-hydroxyphenyl] -cyclohexanol) 5- (1,1-Dimethyloctyl) -2 - [(1 RS , 3 SR ) -3-hydroxycyclohexyl] phenol
CP-47,497-C9 homolog ( cis -3- [4- (1,1-Dimethylnonyl) -2-hydroxyphenyl] -cyclohexanol) 5- (1,1-Dimethylnonyl) -2 - [(1 RS , 3 SR ) -3-hydroxycyclohexyl] phenol

On January 19, 2009, employees of the University of Freiburg announced that u. a. "A chemically slightly modified form (analogue) of the synthetic cannabinoid CP-47,497" is one of the effective ingredients of the drug Spice .

Legal position

  • Germany : With effect from January 22, 2009, CP-47,497 was classified in Germany as a marketable but not a prescription narcotic by entry in Annex II of the Narcotics Act (BtMG) .
  • Switzerland : With the entry into force of the revised Narcotics Ordinance by Swissmedic on December 1, 2010, CP-47,497 was made subject to the Narcotics Act and was therefore illegal from that point on. Importation, possession, distribution etc. are punished according to the Narcotics Act.

Individual evidence

  1. LS Melvin, MR Johnson, CA Harbert, GM Milne, A. Weissman: A cannabinoid derived prototypical analgesic. In: J. Med. Chem. 27, 1984, pp. 67-71, doi: 10.1021 / jm00367a013 .
  2. This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
  3. ^ A. Weissman, GM Milne, LS Melvin Jr .: Cannabimimetic activity from CP-47,497, a derivative of 3-phenylcyclohexanol. In: Journal of Pharmacology and Experimental Therapeutics . tape 223 , no. 2 , November 1982, pp. 516-523 ( aspetjournals.org [accessed January 19, 2009]).
  4. JY Shim, WJ Welsh, AC Howlett: Homology model of the CB1 cannabinoid receptor: sites critical for nonclassical cannabinoid agonist interaction. In: Biopolymers . 71 (2), 2003, pp. 169-189. PMID 12767117 .
  5. Roger Pertwee: Cannabinoids. (= Handbook of Experimental Pharmacology. Vol. 168). Springer, 2005, ISBN 3-540-22565-X .
  6. PJ Little, DR Compton, MR Johnson, LS Melvin, BR Martin: Pharmacology and stereoselectivity of structurally novel cannabinoids in mice. In: Journal of Pharmacology and Experimental Therapeutics . 247, 1988, pp. 1046-1051.
  7. Appendix II to the BtMG
  8. Main active ingredient of "Spice" identified. University of Freiburg.
  9. 22nd BtMÄndV of January 19, 2009 ( BGBl. I p. 49 ).
  10. Text of the Swissmedic Narcotics Ordinance, which came into force on December 1, 2010, as a PDF .
  11. Text of the Swiss Narcotics Act as PDF. Relevant criminal provisions: Art. 19 and following.