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07-SEPTEMBER-2008 03:17:44 - Dimethylheptylpyran Dimethylheptylpyran Systematic IUPAC name 6,6,9-trimethyl-3-3-methyloctan-2-yl- 7,8,9,10-tetrahydrobenzocchromen-1-ol Identifiers CAS number 32904-22-6 ATC code ? PubChem 36276 Chemical data Formula C25H38O2 Mol. mass 370.57 g/mol Pharmacokinetic data Bioavailability ? Metabolism ? Half life ? Excretion ? Therapeutic considerations Pregnancy cat. ? Legal status Schedule I / Class A Routes ? Dimethylheptylpyran 1,2-dimethylheptyl-Δ3THC, DMHP, EA-1476 is a synthetic analogue of THC, which was invented in 1949 during attempts to elucidate the structure of Δ9-THC, the active component of cannabis.1 Effects DMHP is similar in both structure to THC, differing only in the position of one double bond, and the replacement of the 3-pentyl chain with a 3-1,2-dimethylheptyl chain.2 It produces similar activity to THC, such as sedative effects, but is considerably more potent.3 It is thought to act as a CB1 agonist, in a similar manner to other similar cannabinoid derivatives.4 Legality DMHP was made illegal under UN convention in 1982 on the basis of its structural similarity and similar effects profile to THC, despite never having had any recorded instances of abuse by humans or illicit sale. In the United States, DMHP was placed into the most restrictive Schedule I as a compound with no medical use, although it is still used in some scientific research into cannabinoid drugs. Tablets This pharmacology-related article is a stub. References ^ Adams R, Harfenist M, Loewe S. New Analogs of Tetrahydrocannabinol. XIX. Journal of the American Chemical Society. 1949; 715:1624-1628. ^ Razdan RK. The Total Synthesis of Cannabinoids. Wiley-Interscience 1980. ^ Wilkison DM, Pontzer N, Hosko MJ. Slowing of cortical somatosensory evoked activity by delta 9-tetrahydrocannabinol and dimethylheptylpyran in alpha-chloralose-anesthetized cats. Neuropharmacology. 1982 Jul;217:705-9. PMID 6289158 ^ Parker LA, Mechoulam R. Cannabinoid agonists and antagonists modulate lithium-induced conditioned gaping in rats. Integrative Physiological and Behavioural Science. 2003 Apr-Jun;382:133-45. PMID 14527182 v d e Cannabinoids Plant cannabinoids CBD CBDV CBN CBG CBV CBL THC THC-C4 THCV Cannabinoid metabolites 11-Hydroxy-THC 11-nor-9-Carboxy-THC Endogenous cannabinoids Arachidonoyl ethanolamide Anandamide or AEA 2-Arachidonoylglycerol 2-AG 2-Arachidonyl glyceryl ether noladin ether Virodhamine N-arachidonoyl-dopamine NADA; Oleamide Synthetic cannabinoid agonists Classical cannabinoids Dibenzopyrans A-41988 Ajulemic acid AM-087 AM-411 AM-855 AM-905 AM-906 AM-919 AM-938 AM-4030 AMG-1 AMG-3 AMG-36 AMG-41 Dexanabinol HU-211 DMHP Dronabinol HU-210 JWH-051 JWH-133 JWH-139 L-759,633 L-759,656 Levonantradol Nabilone Nabitan O-806 O-823 O-1057 O-1125 O-1238 O-2545 O-2694 Parahexyl THC-O-acetate THC-O-phosphate Nonclassical cannabinoids CP 47,497 CP 55,244 CP 55,940 HU-308 2-Isopropyl-5-methyl-1-2,6-dihydroxy-4-nonylphenylcyclohex-1-ene Aminoalkylindoles AM-630 AM-1241 JWH-015 JWH-018 JWH-073 JWH-081 JWH-200 L-768,242 Pravadoline WIN 55,212-2 Aminoalkylpyrroles JWH-030 JWH-147 JWH-307 Eicosanoids AM-883 Arachidonyl-2'-chloroethylamide Arachidonylcyclopropylamide Methanandamide O-585 O-689 O-1812 O-1860 O-1861 Others BAY 38-7271 BAY 59-3074 GW 842,166X JWH-171 O-2220 Endocannabinoid activity enhancers AM-404 CAY-10401 CAY-10402 N-arachidonoyl-serotonin O-1624 PF-622 PF-750 URB-597 URB-602 URB-754 Cannabinoid antagonists and inverse agonists AM-251 AM-281 AM-630 AVE-1625 BML-190 CAY-10508 CB-25 CB-52 JTE-907 LY-320,135 MK-9470 NESS-0327 O-1184 O-2050 O-2654 Rimonabant SLV-319 SR-144,528 Surinabant Taranabant VCHSR Retrieved from http://en..org/wiki/Dimethylheptylpyran Categories: Pharmacology stubs | Cannabinoids Views Article Discussion this page History Personal tools Log in / create account Navigation Main page Contents Featured content Current events Random article Search Go Search Interaction Community portal Recent changes Contact Donate to Help Toolbox What links here Related changes Upload file Special pages Printable version Permanent link Cite this page This page was last modified on 3 August 2008, at 06:1
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