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Substance Name: Pyrilamine maleate [USAN:USP]
RN: 59-33-6
UNII: R35D29L3ZA
InChIKey: JXYWFNAQESKDNC-BTJKTKAUSA-N

Note

  • A histamine H1 antagonist. It has mild hypnotic properties and some local anesthetic action and is used for allergies (including skin eruptions) both parenterally and locally. It is a common ingredient of cold remedies.

Molecular Formula

  • C17-H23-N3-O.C4-H4-O4

Molecular Weight

  • 401.4603
 

Classification Codes

  • Antihistaminic
  • Drug / Therapeutic Agent
  • Human Data
  • Mutation Data
  • Reproductive Effect
  • Tumor Data
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Names and Synonyms

Name of Substance

  • Pyrilamine maleate [USAN:USP]

Synonyms

  • 1,2-Ethanediamine, N-((4-methoxyphenyl)methyl)-N',N'-dimethyl-N-2-pyridinyl-, (Z)-2-butenedioate (1:1)
  • 2-((2-(Dimethylamino)ethyl)(p-methoxybenzyl)amino)pyridine maleate (1:1)
  • 2786 R.P. maleate
  • Anisopyradamine
  • Anthisan maleate
  • Antihist
  • CCRIS 1330
  • Diaminide maleate
  • Dorantamin maleate
  • EINECS 200-422-7
  • Histan
  • Histatex
  • Histavet-P (veterinary)
  • Histine
  • Histosol
  • Kriptin maleate
  • Mepyramine hydrogen maleinate
  • Mepyramine maleate
  • Minihist
  • N,N-Dimethyl-N'-(4-methoxybenzyl)-N'-(2-pyridyl)ethylenediamine maleate
  • N-Dimethylaminoethyl-N-p-methoxy-alpha-aminopyridine maleate
  • N-p-Methoxybenzyl-N',N'-dimethyl-N-alpha-pyridylethylenediamine maleate
  • Neo-Antergan maleate
  • Neoantergan maleate
  • NSC 3604
  • Paramal
  • Paraminyl maleate
  • Prefrin A
  • Pymafed
  • Pyra maleate
  • Pyra-Maleate
  • Pyramal maleate
  • Pyranilamine maleate
  • Pyraninyl
  • Pyranisamine maleate
  • Pyrilamine maleate
  • Renstamin
  • Stangen maleate
  • Statomin maleate
  • Thylogen maleate
  • UNII-R35D29L3ZA

Systematic Names

  • 1,2-Ethanediamine, N-((4-methoxyphenyl)methyl)-N',N'-dimethyl-N-2-pyridinyl-, (2Z)-2-butenedioate (1:1)
  • 1,2-Ethanediamine, N-((4-methoxyphenyl)methyl)-N',N'-dimethyl-N-2-pyridinyl-, (Z)-2-butenedioate (1:1)
  • 1,2-Ethanediamine, N1-((4-methoxyphenyl)methyl)-N2,N2-dimethyl-N1-2-pyridinyl-, (2Z)-2-butenedioate (1:1)
  • Mepyramine maleate
  • Pyridine, 2-((2-(dimethylamino)ethyl)(p-methoxybenzyl)amino)-, maleate (1:1)
  • Pyrilamine maleate

Mixture Names

  • 4-Way Nasal Spray Regular and Menthol
  • Endotussin-NN
  • Histalet Forte
  • Midol Maximum Strength
  • Midol Maximum Strength PMS
  • Midol Regular Strength
  • PV Tussin Syrup
  • Robitussin Night Relief
  • Ru-Tuss Hydrocodone Liquid
  • Viravan

Registry Numbers

CAS Registry Number

  • 59-33-6

FDA UNII

  • R35D29L3ZA

Other Registry Number

  • 5572-06-5

System Generated Number

  • 0000059336

Molecular Formulas

Molecular Formula

  • C17-H23-N3-O.C4-H4-O4

Molecular Formula Fragments

  • C17-H23-N3-O
  • C4-H4-O4
  • COMPONENT

Structure Descriptors

InChI

InChI=1S/C17H23N3O.C4H4O4/c1-19(2)12-13-20(17-6-4-5-11-18-17)14-15-7-9-16(21-3)10-8-15;5-3(6)1-2-4(7)8/h4-11H,12-14H2,1-3H3;1-2H,(H,5,6)(H,7,8)/b;2-1-

InChIKey

JXYWFNAQESKDNC-BTJKTKAUSA-N

Smiles

COc1ccc(CN(CCN(C)C)c2ccccn2)cc1.OC(=O)\C=C/C(=O)O

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
child LDLo oral 42mg/kg (42mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA

GASTROINTESTINAL: NAUSEA OR VOMITING
Lancet. Vol. 2, Pg. 809, 1952.
guinea pig LD50 intravenous 24400ug/kg (24.4mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 113, Pg. 313, 1958.
guinea pig LD50 subcutaneous 44mg/kg (44mg/kg)   Annales Pharmaceutiques Francaises. Vol. 20, Pg. 463, 1962.
mouse LD50 intraperitoneal 100mg/kg (100mg/kg)   Planta Medica. Vol. 42, Pg. 75, 1981.
mouse LD50 intravenous 23mg/kg (23mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 155, Pg. 47, 1965.
mouse LD50 oral 220mg/kg (220mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 155, Pg. 47, 1965.
mouse LD50 subcutaneous 141mg/kg (141mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 14, Pg. 940, 1964.
rat LD50 oral 513mg/kg (513mg/kg)   Toxicology and Applied Pharmacology. Vol. 1, Pg. 42, 1959.
rat LDLo subcutaneous 150mg/kg (150mg/kg) BEHAVIORAL: TREMOR Comptes Rendus des Seances de la Societe de Biologie et de Ses Filiales. Vol. 144, Pg. 887, 1950.
women TDLo oral 200mg/kg (200mg/kg) VASCULAR: BP ELEVATION NOT CHARACTERIZED IN AUTONOMIC SECTION

CARDIAC: OTHER CHANGES

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
JAMA, Journal of the American Medical Association. Vol. 257, Pg. 660, 1987.