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Substance Name: Mescaline
RN: 54-04-6
UNII: RHO99102VC
InChIKey: RHCSKNNOAZULRK-UHFFFAOYSA-N

Note

  • Hallucinogenic alkaloid isolated from the flowering heads (peyote) of Lophophora (formerly Anhalonium) williamsii, a Mexican cactus used in Indian religious rites and as an experimental psychotomimetic. Among its cellular effects are agonist actions at some types of serotonin receptors. It has no accepted therapeutic uses although it is legal for religious use by members of the Native American Church.

Molecular Formula

  • C11-H17-N-O3

Molecular Weight

  • 211.2593
 

Classification Codes

Classification Codes

  • Central Nervous System Agents
  • Drug / Therapeutic Agent
  • Hallucinogens
  • Human Data
  • Neurotransmitter Agents
  • Psychotropic Drugs
  • Reproductive Effect
  • Serotonin Agents
  • Serotonin Receptor Agonists

Superlist Classification Code

  • DEA Schedule I
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Names and Synonyms

Results Name

  • Mescaline

Name of Substance

  • 3,4,5-Trimethoxyphenethylamine
  • Mescaline

MeSH Heading

  • Mescaline

Synonyms

  • 3,4,5-Trimethoxybenzeneethanamine
  • 3,4,5-Trimethoxyphenethylamine
  • 3,4,5-Trimethoxyphenylethylamine
  • 4-13-00-02919 (Beilstein Handbook Reference)
  • Benzeneethanamine, 3,4,5-trimethoxy-
  • BRN 1374088
  • EINECS 200-190-7
  • Ethane, 1-amino-2-(3,4,5-trimethoxyphenyl)-
  • HSDB 7503
  • Mescalin
  • Mescalin [German]
  • Mescaline
  • Mezcaline
  • NSC 30419
  • Tmpea
  • UNII-RHO99102VC

Systematic Names

  • 3,4,5-Trimethoxyphenethylamine
  • Benzeneethanamine, 3,4,5-trimethoxy-
  • Phenethylamine, 3,4,5-trimethoxy-

Superlist Names

  • Constituent of Peyote cacti
  • DEA No. 7381
  • Mescaline

Registry Numbers

CAS Registry Number

  • 54-04-6

FDA UNII

  • RHO99102VC

System Generated Number

  • 0000054046

Structure Descriptors

InChI

1S/C11H17NO3/c1-13-9-6-8(4-5-12)7-10(14-2)11(9)15-3/h6-7H,4-5,12H2,1-3H3

InChIKey

RHCSKNNOAZULRK-UHFFFAOYSA-N

Smiles

COc1cc(CCN)cc(OC)c1OC

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
frog LDLo parenteral 750mg/kg (750mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA

PERIPHERAL NERVE AND SENSATION: SPASTIC PARALYSIS WITH OR WITHOUT SENSORY CHANGE
Journal of Pharmacology and Experimental Therapeutics. Vol. 50, Pg. 359, 1934.
guinea pig LDLo subcutaneous 500mg/kg (500mg/kg) PERIPHERAL NERVE AND SENSATION: SPASTIC PARALYSIS WITH OR WITHOUT SENSORY CHANGE

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Journal of Pharmacology and Experimental Therapeutics. Vol. 50, Pg. 359, 1934.
human TDLo intramuscular 2500ug/kg (2.5mg/kg) BEHAVIORAL: EUPHORIA

BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"
Psychopharmacologia Vol. 3, Pg. 219, 1962.
mouse LD50 intraperitoneal 315mg/kg (315mg/kg)   Journal of Medicinal Chemistry. Vol. 13, Pg. 26, 1970.
mouse LD50 intravenous 157mg/kg (157mg/kg)   Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 64, Pg. 159, 1968.
mouse LD50 oral 880mg/kg (880mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 131, Pg. 115, 1961.
mouse LD50 subcutaneous 534mg/kg (534mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION

GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS
Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 58, Pg. 261, 1962.
mouse LD50 unreported 261mg/kg (261mg/kg) BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)
Nature. Vol. 218, Pg. 298, 1968.
rat LD50 intramuscular 330mg/kg (330mg/kg)   Pharmazie in Unserer Zeit. Vol. 14, Pg. 129, 1985.
rat LD50 intravenous 157mg/kg (157mg/kg)   Pharmazie in Unserer Zeit. Vol. 14, Pg. 129, 1985.
rat LD50 subcutaneous 534mg/kg (534mg/kg)   Pharmazie in Unserer Zeit. Vol. 14, Pg. 129, 1985.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 35.5 deg C   EXP
pKa Dissociation Constant 9.56 (none)   EXP
log P (octanol-water) 0.78 (none)   EXP
Water Solubility 8.41E+04 mg/L 25 EST
Vapor Pressure 3.22E-04 mm Hg 25 EST
Henry's Law Constant 1.68E-10 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 2.35E-10 cm3/molecule-sec 25 EST

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