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Substance Name: Trimethaphan camsylate [USP]
RN: 68-91-7
UNII: 8W556014K9
InChIKey: HALWUDBBYKMYPW-STOWLHSFSA-M

Note

  • A nicotinic antagonist that has been used as a ganglionic blocker in hypertension, as an adjunct to anesthesia, and to induce hypotension during surgery.

Molecular Formula

  • C22-H25-N2-O-S.C10-H15-O4-S

Molecular Weight

  • 596.809
 

Classification Codes

  • Antihypertensive
  • Cardiovascular Agents
  • Drug / Therapeutic Agent
  • Vasodilator Agents
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Names and Synonyms

Name of Substance

  • Trimetaphan camsilate [INN:BAN:JAN]
  • Trimethaphan camsylate
  • Trimethaphan camsylate [USP]

Synonyms

  • (+)-1,3-Dibenzyldecahydro-2-oxoimidazo(4,5-c)thieno(1,2-a)-thiolium 2-oxo-10-bornanesulfonate (1:1)
  • 1,3-Dibenzyldecahydro-2-oxo-imidazo(4,5-c)thieno(1,2-a)thiolium 2-oxo-10-boranesulfonate
  • 1,3-Dibenzyldecahydro-2-oxoimidazo(4,5-c)thieno(1,2-a)thiolium 10-camphorsulfonate
  • Arfonad
  • Arphonad
  • Camfosulfonato del d-3-4-(1'dibenzil-2-cheto-imidazolido)-1,2-trimetilthiophanium
  • Camfosulfonato del d-3-4-(1'dibenzil-2-cheto-imidazolido)-1,2-trimetilthiophanium [Italian]
  • Camphosulfonate de trimetaphan
  • Camsilate de trimetaphan
  • Camsilate de trimetaphan [INN-French]
  • Cansilato de trimetafano
  • Cansilato de trimetafano [INN-Spanish]
  • d-3,4-(1',3'-Dibenzyl-2'-ketoimidazolido)-1,2-trimethylenethiophanium d-camphorsulfonate
  • EINECS 200-696-8
  • NU 2222
  • Ro 2-2222
  • Thieno(1',2':1,2)thieno(3,4-d)imidazol-5-ium, decahydro-2-oxo-1,3-bis(phenylmethyl)-, salt with (+)-7,7-dimethyl-2-oxobicyclo(2.2.1)heptane-1-methanesulfonic acid (1:1)
  • Trimetaphan camphorsulfonate
  • Trimetaphan camsilate
  • Trimetaphan camsylate
  • Trimetaphani camsilas
  • Trimetaphani camsilas [INN-Latin]
  • Trimethaphan 10-camphorsulfonate
  • Trimethaphan camphorsulfonate
  • Trimethaphan camsylate
  • UNII-8W556014K9

Systematic Names

  • Decahydro-2-oxo-1,3-bis(phenylmethyl)thieno(1',2':1,2) thieno(3,4-d)imidazol-5-ium, salt with (1S)-7,7-dimethyl-2-oxobicyclo(2.2.1)heptane-1-methanesulfon ic acid (1:1)
  • Imidazo(4,5-c)thieno(1,2-a)thiolium, 1,3-dibenzyldecahydro-2-oxo-, 2-oxo-10-boranesulfonate
  • Thieno(1',2':1,2)thieno(3,4-d)imidazol-5-ium, decahydro-2-oxo-1,3-bis(phenylmethyl)-, salt with (+)-7,7-dimethyl-2-oxobicyclo(2.2.1)heptane-1-methanesulfonic acid (1:1)
  • Trimetaphan camsilate

Registry Numbers

CAS Registry Number

  • 68-91-7

FDA UNII

  • 8W556014K9

System Generated Number

  • 0000068917

Molecular Formulas

Molecular Formula

  • C22-H25-N2-O-S.C10-H15-O4-S

Molecular Formula Fragments

  • C10-H15-O4-S
  • C22-H25-N2-O-S
  • COMPONENT

Structure Descriptors

InChI

1S/C22H25N2OS.C10H16O4S/c25-22-23(14-17-8-3-1-4-9-17)19-16-26-13-7-12-20(26)21(19)24(22)15-18-10-5-2-6-11-18;1-9(2)7-3-4-10(9,8(11)5-7)6-15(12,13)14/h1-6,8-11,19-21H,7,12-16H2;7H,3-6H2,1-2H3,(H,12,13,14)/q+1;/p-1/t;7-,10-/m.1/s1

InChIKey

HALWUDBBYKMYPW-STOWLHSFSA-M

Smiles

CC1(C)[C@@H]2CC[C@@]1(CS(=O)(=O)[O-])C(=O)C2.O=C3N(Cc4ccccc4)C5C[S+]6CCCC6C5N3Cc7ccccc7

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 intramuscular 8mg/kg (8mg/kg) BLOOD: HEMORRHAGE Journal of Pharmacology and Experimental Therapeutics. Vol. 97, Pg. 48, 1949.
dog LD50 intravenous 750ug/kg (0.75mg/kg) BLOOD: HEMORRHAGE Journal of Pharmacology and Experimental Therapeutics. Vol. 97, Pg. 48, 1949.
dog LD50 oral 400mg/kg (400mg/kg) BLOOD: HEMORRHAGE Journal of Pharmacology and Experimental Therapeutics. Vol. 97, Pg. 48, 1949.
guinea pig LD50 intravenous 13mg/kg (13mg/kg) BLOOD: NORMOCYTIC ANEMIA

KIDNEY, URETER, AND BLADDER: OTHER CHANGES

VASCULAR: ACUTE ARTERIAL OCCLUSION
Farmaco, Edizione Scientifica. Vol. 10, Pg. 1027, 1955.
monkey LD50 intravenous > 8mg/kg (8mg/kg)   Farmaco, Edizione Scientifica. Vol. 10, Pg. 1027, 1955.
mouse LD50 intramuscular 133mg/kg (133mg/kg)   Yakkyoku. Pharmacy. Vol. 28, Pg. 495, 1977.
mouse LD50 intraperitoneal 32400ug/kg (32.4mg/kg)   Russian Pharmacology and Toxicology Vol. 37, Pg. 7, 1974.
mouse LD50 intravenous 14400ug/kg (14.4mg/kg)   Russian Pharmacology and Toxicology Vol. 37, Pg. 7, 1974.
mouse LD50 oral 927mg/kg (927mg/kg) BEHAVIORAL: TREMOR

GASTROINTESTINAL: NAUSEA OR VOMITING

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Toho Igakkai Zasshi. Journal of Medical Society of Toho University. Vol. 19, Pg. 727, 1972.
mouse LD50 subcutaneous 692mg/kg (692mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) Toho Igakkai Zasshi. Journal of Medical Society of Toho University. Vol. 19, Pg. 727, 1972.
rabbit LD50 intravenous 23mg/kg (23mg/kg) VASCULAR: ACUTE ARTERIAL OCCLUSION

BLOOD: NORMOCYTIC ANEMIA

KIDNEY, URETER, AND BLADDER: OTHER CHANGES
Farmaco, Edizione Scientifica. Vol. 10, Pg. 1027, 1955.
rat LD50 intramuscular 141mg/kg (141mg/kg)   Yakkyoku. Pharmacy. Vol. 28, Pg. 495, 1977.
rat LD50 intraperitoneal 141mg/kg (141mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

GASTROINTESTINAL: NAUSEA OR VOMITING
Toho Igakkai Zasshi. Journal of Medical Society of Toho University. Vol. 19, Pg. 727, 1972.
rat LD50 intravenous 21mg/kg (21mg/kg)   Compilation of LD50 Values of New Drugs.
rat LD50 oral 2494mg/kg (2494mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING

BEHAVIORAL: TREMOR

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Toho Igakkai Zasshi. Journal of Medical Society of Toho University. Vol. 19, Pg. 727, 1972.
rat LD50 subcutaneous 2024mg/kg (2024mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

GASTROINTESTINAL: NAUSEA OR VOMITING
Toho Igakkai Zasshi. Journal of Medical Society of Toho University. Vol. 19, Pg. 727, 1972.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 245 dec deg C   EXP
log P (octanol-water) 6.860 (none)   EST
Atmospheric OH Rate Constant 6.49E-11 cm3/molecule-sec 25 EST

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