TCI

(6aR,10aR)-6,6,9-trimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromen-1-ol

Created: 2010-02-23
Last modified:  2021-03-01

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Chemical Details

Formal Charge0
Atom Count53
Chiral Atom Count2
Bond Count55
Aromatic Bond Count6
2D diagram of TCI

Chemical Component Summary

Name(6aR,10aR)-6,6,9-trimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromen-1-ol
SynonymsTetrahydrocannabinol
Systematic Name (OpenEye OEToolkits)(6aR,10aR)-6,6,9-trimethyl-3-pentyl-6a,7,8,10a-tetrahydrobenzo[c]isochromen-1-ol
FormulaC21 H30 O2
Molecular Weight314.462
TypeNON-POLYMER

Chemical Descriptors

TypeProgram Version Descriptor
SMILESCACTVS3.352CCCCCc1cc(O)c2[CH]3C=C(C)CC[CH]3C(C)(C)Oc2c1
SMILESOpenEye OEToolkits1.7.0CCCCCc1cc(c2c(c1)OC(C3C2C=C(CC3)C)(C)C)O
Canonical SMILESCACTVS3.352 CCCCCc1cc(O)c2[C@@H]3C=C(C)CC[C@H]3C(C)(C)Oc2c1
Canonical SMILESOpenEye OEToolkits1.7.0 CCCCCc1cc(c2c(c1)OC([C@H]3[C@H]2C=C(CC3)C)(C)C)O
InChIInChI1.03 InChI=1S/C21H30O2/c1-5-6-7-8-15-12-18(22)20-16-11-14(2)9-10-17(16)21(3,4)23-19(20)13-15/h11-13,16-17,22H,5-10H2,1-4H3/t16-,17-/m1/s1
InChIKeyInChI1.03 CYQFCXCEBYINGO-IAGOWNOFSA-N

Drug Info: DrugBank

DrugBank IDDB00470 
NameDronabinol
Groups
  • approved
  • illicit
DescriptionDronabinol (marketed as Marinol) is a synthetic form of delta-9-tetrahydrocannabinol (Δ⁹-THC), the primary psychoactive component of cannabis (marijuana). THC demonstrates its effects through weak partial agonist activity at Cannabinoid-1 (CB1R) and Cannabinoid-2 (CB2R) receptors, which results in the well-known effects of smoking cannabis such as increased appetite, reduced pain, and changes in emotional and cognitive processes. Due to its evidence as an appetite stimulant and an anti-nauseant, Dronabinol is approved for use in anorexia associated with weight loss in patients with AIDS and for the treatment of nausea and vomiting associated with cancer chemotherapy in patients who have failed to respond adequately to conventional antiemetic treatments [FDA Label]. Tetrahydrocannabinol (THC) and cannabidiol (CBD) are the two most abundant cannabinoids found naturally in the resin of the marijuana plant, both of which are pharmacologically active due to their interaction with cannabinoid receptors that are found throughout the body [A32830]. While both CBD and THC are used for medicinal purposes, they have different receptor activity, function, and physiological effects. If not provided in their activated form (such as through synthetic forms like Dronabinol or [DB00486]), THC and CBD are obtained through conversion from their precursors, tetrahydrocannabinolic acid-A (THCA-A) and cannabidiolic acid (CBDA), through decarboxylation reactions. This can be achieved through heating, smoking, vaporization, or baking of dried unfertilized female cannabis flowers. From a pharmacological perspective, Cannabis' diverse receptor profile explains its potential application for such a wide variety of medical conditions. Cannabis contains more than 400 different chemical compounds, of which 61 are considered cannabinoids, a class of compounds that act upon endogenous cannabinoid receptors of the body [A32584]. The endocannabinoid system is widely distributed throughout the central and peripheral nervous system (via the Cannabinoid Receptors CB1 and CB2) and plays a role in many physiological processes such as inflammation, cardiovascular function, learning, pain, memory, stress and emotional regulation, and the sleep/wake cycle among many others [A32824]. CB1 receptors are found in both the central and peripheral nervous system, and are most abundant in the hippocampus and amygdala, which are the areas of the brain responsible for short-term memory storage and emotional regulation. CB2 receptors are mainly located in the peripheral nervous system and can be found on lymphoid tissue where they are involved in regulation of immune function [A32676].
Synonyms
  • Δ9-tetrahydrocannabinol
  • delta9-tetrahydrocannabinol
  • delta-9-tetrahydrocannabinol
  • 6,6,9-Trimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromen-1-ol
  • THC
Brand Names
  • Dronabinol
  • Sativex
  • Marinol Cap 10mg
  • Syndros
  • Marinol
IndicationDronabinol is indicated for the treatment of anorexia associated with weight loss in patients with AIDS, and nausea and vomiting associated with cancer chemotherapy in patients who have failed to respond adequately to conventional antiemetic treatments.[L43438]
Categories
  • Agents producing tachycardia
  • Alimentary Tract and Metabolism
  • Analgesics
  • Analgesics, Non-Narcotic
  • Antiemetics and Antinauseants
ATC-CodeA04AD10
CAS number1972-08-3

Drug Targets

NameTarget SequencePharmacological ActionActions
Cannabinoid receptor 1MKSILDGLADTTFRTITTDLLYVGSNDIQYEDIKGDMASKLGYFPQKFPL...unknownagonist
Cannabinoid receptor 2MEECWVTEIANGSKDGLDSNPMKDYMILSGPQKTAVAVLCTLLGLLSALE...unknownagonist
Cytochrome P450 1A1MLFPISMSATEFLLASVIFCLVFWVIRASRPQVPKGLKNPPGPWGWPLIG...unknowninhibitor,inducer
Cytochrome P450 1A2MALSQSVPFSATELLLASAIFCLVFWVLKGLRPRVPKGLKSPPEPWGWPL...unknowninhibitor
Cytochrome P450 1B1MGTSLSPNDPWPLNPLSIQQTTLLLLLSVLATVHVGQRLLRQRRRQLRSA...unknowninhibitor
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Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
Pharos CHEMBL465
PubChem 16078
ChEMBL CHEMBL465
ChEBI CHEBI:66964