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Substance Name: Levomepromazine [USAN:INN:BAN:DCF]
RN: 60-99-1
UNII: 9G0LAW7ATQ
InChIKey: VRQVVMDWGGWHTJ-CQSZACIVSA-N

Note

  • A phenothiazine with pharmacological activity similar to that of both CHLORPROMAZINE and PROMETHAZINE. It has the histamine-antagonist properties of the antihistamines together with CENTRAL NERVOUS SYSTEM effects resembling those of chlorpromazine. (From Martindale, The Extra Pharmacopoeia, 30th ed, p604).

Molecular Formula

  • C19-H24-N2-O-S

Molecular Weight

  • 328.4776
 

Classification Codes

  • Analgesic
  • Analgesic (Central Nervous System Depressant)
  • Analgesics
  • Analgesics, Non-Narcotic
  • Antipsychotic Agents
  • Central Nervous System Agents
  • Central Nervous System Depressants
  • Dopamine Agents
  • Dopamine Antagonists
  • Drug / Therapeutic Agent
  • Human Data
  • Neurotransmitter Agents
  • Peripheral Nervous System Agents
  • Psychotropic Drugs
  • Sensory System Agents
  • Tranquilizing Agents
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Names and Synonyms

Name of Substance

  • Levomepromazine [USAN:INN:BAN:DCF]
  • Methotrimeprazine
  • Methotrimeprazine [USP]

MeSH Heading

  • Methotrimeprazine

Synonyms

  • (-)-(2R)-3-(2-Methoxy-10H-phenothiazin-10-yl)-N,N,2-trimethylpropan-1-amine
  • (-)-10-(3-(Dimethylamino)-2-methylpropyl)-2-methoxyphenothiazine
  • 10H-Phenothiazine-10-propanamine, 2-methoxy-N,N,beta-trimethyl-, (betaR)-
  • 10H-Phenothiazine-10-propanamine, 2-methoxy-N,N,beta-trimethyl-, (R)-
  • 2-Methoxytrimeprazine
  • 7044 R.P.
  • Arc-VI-C-5
  • Bayer 1213
  • CL 36467
  • CL 39743
  • CL 53212
  • Dedoran
  • EINECS 200-495-5
  • Hirnamin
  • Hirnamine
  • Levomeprazine
  • Levomepromazin
  • Levomepromazina
  • Levomepromazina [INN-Spanish]
  • Levomepromazine
  • Levomepromazinum
  • Levomepromazinum [INN-Latin]
  • Levopromazine
  • Levopromazioni
  • Levoprome
  • Levopromethazine
  • Levotomin
  • Mepromazine
  • Methotrimeprazine
  • Methoxytrimeprazine
  • Milezin
  • Minozinan
  • Neozine
  • Neurocil
  • Nirnamine
  • Nirvan
  • Nocinan
  • Nomizan
  • Nozinan
  • Nozinane
  • NSC 226516
  • RP 7044
  • RP-7044
  • Sinogan
  • Sinogan-debil
  • SK&F 5116
  • SKF 5116
  • Tisercin
  • UNII-9G0LAW7ATQ
  • Veractil
  • XP03

Systematic Names

  • 10H-Phenothiazine-10-propanamine, 2-methoxy-N,N,beta-trimethyl-, (-)-
  • 10H-Phenothiazine-10-propanamine, 2-methoxy-N,N,beta-trimethyl-, (R)-
  • Levomepromazine
  • Phenothiazine, 10-(3-(dimethylamino)-2-methylpropyl)-2-methoxy-, (-)-

Registry Numbers

CAS Registry Number

  • 60-99-1

FDA UNII

  • 9G0LAW7ATQ

System Generated Number

  • 0000060991

Structure Descriptors

InChI

InChI=1S/C19H24N2OS/c1-14(12-20(2)3)13-21-16-7-5-6-8-18(16)23-19-10-9-15(22-4)11-17(19)21/h5-11,14H,12-13H2,1-4H3/t14-/m1/s1

InChIKey

VRQVVMDWGGWHTJ-CQSZACIVSA-N

Smiles

COc1ccc2Sc3ccccc3N(C[C@H](C)CN(C)C)c2c1

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
bird - wild LD50 oral 100mg/kg (100mg/kg)   Toxicology and Applied Pharmacology. Vol. 21, Pg. 315, 1972.
man TDLo oral 7143ug/kg (7.143mg/kg) BLOOD: THROMBOCYTOPENIA Human Psychopharmacology. Vol. 9, Pg. 299, 1994.
mouse LD50 intraperitoneal 58500ug/kg (58.5mg/kg)   Farmakologiya i Toksikologiya Vol. 53(4), Pg. 19, 1990.
mouse LD50 intravenous 39mg/kg (39mg/kg)   Proceedings of the European Society for the Study of Drug Toxicity. Vol. 9, Pg. 159, 1968.
mouse LD50 oral 370mg/kg (370mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 15, Pg. 841, 1965.
mouse LD50 subcutaneous 300mg/kg (300mg/kg)   Psychopharmacology Service Center, Bulletin. Vol. 2, Pg. 17, 1963.
rat LD50 oral 1100mg/kg (1100mg/kg)   "Psychotropic Drugs and Related Compounds," 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972Vol. -, Pg. 31, 1972.
rat LD50 subcutaneous 45mg/kg (45mg/kg)   "Psychotropic Drugs and Related Compounds," 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972Vol. -, Pg. 31, 1972.

Physical Properties

Physical Property Value Units Temp (deg C) Source
pKa Dissociation Constant 9.19 (none)   EXP
log P (octanol-water) 4.68 (none)   EXP
Water Solubility 20 mg/L 25 EXP
Vapor Pressure 9.20E-08 mm Hg 25 EST
Henry's Law Constant 3.91E-11 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 2.94E-10 cm3/molecule-sec 25 EST

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