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Substance Name: Dronabinol [USAN:USP:INN]
RN: 1972-08-3
UNII: 7J8897W37S
InChIKey: CYQFCXCEBYINGO-IAGOWNOFSA-N

Note

  • A psychoactive compound extracted from the resin of Cannabis sativa (marihuana, hashish). The isomer delta-9-tetrahydrocannabinol (THC) is considered the most active form, producing characteristic mood and perceptual changes associated with this compound.

Molecular Formula

  • C21-H30-O2

Molecular Weight

  • 314.466
 

Classification Codes

Classification Codes

  • Analgesics
  • Analgesics, Non-Narcotic
  • Anti-Emetic
  • Cannabinoid Receptor Agonists
  • Cannabinoid Receptor Modulators
  • Central Nervous System Agents
  • Drug / Therapeutic Agent
  • Hallucinogens
  • Hormones
  • Hormones, Hormone Substitutes, and Hormone Antagonists
  • Mutation Data
  • Natural Product
  • Neurotransmitter Agents
  • Peripheral Nervous System Agents
  • Psychotropic Drugs
  • Reproductive Effect
  • Sensory System Agents
  • Tumor Data

Superlist Classification Codes

  • DEA Schedule I
  • DEA Schedule III

Names and Synonyms

Name of Substance

  • delta 9-Tetrahydrocannabinol
  • Dronabinol
  • Dronabinol [USAN:USP:INN]

MeSH Heading

  • Dronabinol

Synonyms

  • (-)-delta(sup 1)-3,4-trans-Tetrahydrocannabinol
  • (-)-delta9-trans-Tetrahydrocannabinol
  • (6aR,10aR)-6a,7,8,10a-Tetrahydro-6,6,9-trimethyl-3-pentyl-6H-dibenzo(b,d)pyran-1-ol
  • (l)-delta(sup 1)-Tetrahydrocannabinol
  • 1-trans-delta(sup 9)-Tetrahydrocannabinol
  • 1-trans-delta-9-Tetrahydrocannabinol
  • 3-Pentyl-6,6,9-trimethyl-6a,7,8,10a-tetrahydro-6H-dibenzo(b,d)pyran-1-ol
  • 6,6,9-Trimethyl-3-pentyl-7,8,9,10-tetrahydro-6H-dibenzo(b,d)pyran-1-ol
  • 6H-Dibenzo(b,d)pyran-1-ol, 6a,7,8,10a-tetrahydro-6,6,9-trimethyl-3-pentyl-, (6aR-trans)-
  • Abbott 40566
  • Cannabinol, 1-trans-delta(sup 9)-tetrahydro-
  • Cannabinol, delta1-tetrahydro-
  • CCRIS 4726
  • delta(9)-Tetrahydrocannibinol
  • delta(sup 1)-Tetrahydrocannabinol
  • delta(sup 1)-Thc
  • delta(sup 9)-Tetrahydrocannabinol
  • delta(sup 9)-Thc
  • delta-9 Tetrahydrocannabinol
  • delta1-Tetrahydrocannabinol
  • delta1-Tetrahydrocannabinol (VAN)
  • delta1-THC
  • delta9-Tetrahydrocannabinol (VAN)
  • delta9-THC
  • Deltanyne
  • Dronabinol
  • Dronabinolum
  • Dronabinolum [Latin]
  • HSDB 6471
  • l-delta1-trans-Tetrahydrocannabinol
  • Marinol
  • Namisol
  • NSC 134454
  • QCD 84924
  • QCD-84924
  • SP 104
  • Syndros
  • Tetrahydro-6,6,9-trimethyl-3-pentyl-6H-dibenzo(b,d)pyran-1-ol
  • Tetrahydrocannabinol
  • Tetrahydrocannabinols (-)-delta1-3,4-trans-form
  • THC
  • UNII-7J8897W37S

Systematic Names

  • 1-trans-delta9-Tetrahydrocannabinol
  • 6H-Dibenzo(b,d)pyran-1-ol, 6a,7,8,10a-tetrahydro-6,6,9-trimethyl-3-pentyl-, (6aR,10aR)-
  • 6H-Dibenzo(b,d)pyran-1-ol, 6a,7,8,10a-tetrahydro-6,6,9-trimethyl-3-pentyl-, (6aR-trans)-

Superlist Names

  • 1-trans-delta-9-Tetrahydrocannabinol
  • DEA No. 7369
  • Dronabinol in sesame oil in soft gelatin capsule
  • Marinol
  • Synthetic THC in sesame oil / soft gelatin

Registry Numbers

CAS Registry Number

  • 1972-08-3

FDA UNII

  • 7J8897W37S

Other Registry Numbers

  • 1363-19-5
  • 14146-29-3
  • 14146-43-1
  • 26108-45-2
  • 5957-27-7

System Generated Number

  • 0001972083

Structure Descriptors

InChI

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

InChIKey

CYQFCXCEBYINGO-IAGOWNOFSA-N

Smiles

CCCCCc1cc(O)c2[C@@H]3C=C(C)CC[C@H]3C(C)(C)Oc2c1

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LDLo oral 525mg/kg (525mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)

GASTROINTESTINAL: NAUSEA OR VOMITING		 Toxicology and Applied Pharmacology. Vol. 25, Pg. 363, 1973.
monkey LD oral > 3150mg/kg (3150mg/kg)   Toxicology and Applied Pharmacology. Vol. 25, Pg. 363, 1973.
monkey LD50 intravenous 125mg/kg (125mg/kg)   Medical Journal of Australia. Vol. 145, Pg. 82, 1986.
mouse LD50 intracrebral > 12580ug/kg (12.58mg/kg)   Research Communiations in Alcohol and Substances of Abuse. Vol. 17, Pg. 151, 1996.
mouse LD50 intraperitoneal 168mg/kg (168mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: ANALGESIA		 Archives Internationales de Pharmacodynamie et de Therapie. Vol. 196, Pg. 133, 1972.
mouse LD50 intravenous 42mg/kg (42mg/kg) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION

BEHAVIORAL: EXCITEMENT

BEHAVIORAL: ATAXIA		 Annals of the New York Academy of Sciences. Vol. 191, Pg. 74, 1971.
mouse LD50 oral 482mg/kg (482mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

BEHAVIORAL: EXCITEMENT

BEHAVIORAL: TREMOR		 Proceedings of the Society for Experimental Biology and Medicine. Vol. 136, Pg. 260, 1971.
mouse LD50 subcutaneous > 11gm/kg (11000mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 88, Pg. 154, 1946.
rat LD50 intraperitoneal 373mg/kg (373mg/kg) BEHAVIORAL: TREMOR

BEHAVIORAL: EXCITEMENT

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"		 Proceedings of the Society for Experimental Biology and Medicine. Vol. 136, Pg. 260, 1971.
rat LD50 intravenous 29mg/kg (29mg/kg) BEHAVIORAL: EXCITEMENT

BEHAVIORAL: ATAXIA

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION		 Annals of the New York Academy of Sciences. Vol. 191, Pg. 74, 1971.
rat LD50 oral 666mg/kg (666mg/kg) BEHAVIORAL: TREMOR

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

BEHAVIORAL: EXCITEMENT		 Proceedings of the Society for Experimental Biology and Medicine. Vol. 136, Pg. 260, 1971.

Physical Properties

Physical Property Value Units Temp (deg C) Source
pKa Dissociation Constant 10.6 (none)   EXP
log P (octanol-water) 7.600 (none)   EST
Water Solubility 2800 mg/L 23 EXP
Atmospheric OH Rate Constant 3.09E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.