Trimetaphan camsilate

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MedKoo CAT#: 318951

CAS#: 7187-66-8 (camsilate)

Description: Trimetaphan camsilate is a drug that counteracts cholinergic transmission at the ganglion type of nicotinic receptors of the autonomic ganglia and therefore blocks both the sympathetic nervous system and the parasympathetic nervous system. It acts as a non-depolarizing competitive antagonist at the nicotinic acetylcholine receptor, is short-acting, and is given intravenously.

Chemical Structure

Trimetaphan camsilate
CAS# 7187-66-8 (camsilate)

Theoretical Analysis

MedKoo Cat#: 318951
Name: Trimetaphan camsilate
CAS#: 7187-66-8 (camsilate)
Chemical Formula: C32H40N2O5S2
Exact Mass:
Molecular Weight: 596.801
Elemental Analysis: C, 64.40; H, 6.76; N, 4.69; O, 13.40; S, 10.74

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Related CAS #: 7187-66-8 (cation)   7187-66-8 (camsilate)    

Synonym: NU 2222; NU2222; NU-2222; Ro 2-2222; Ro-2-2222; Ro2-2222; Ro 22222; Ro-22222; Ro22222; Trimethaphan; Trimetaphan camsilate; trade name Arfonad.

IUPAC/Chemical Name: 1,3-dibenzyl-2-oxodecahydrothieno[1',2':1,2]thieno[3,4-d]imidazol-5-ium ((1R,4S)-7,7-dimethyl-2-oxobicyclo[2.2.1]heptan-1-yl)methanesulfonate


InChi Code: 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.0/s1

SMILES Code: CC1(C)[C@H]2CC[C@]1(CS(=O)([O-])=O)C(C2)=O.O=C(N3CC4=CC=CC=C4)N(CC5=CC=CC=C5)C6C3C7CCC[S+]7C6

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 596.801 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: Tono T, Ueki Y, Nagata N, Haruta A, Komune S. Effects of trimetaphan-induced deliberate hypotension on human cochlear blood flow. Acta Otolaryngol Suppl. 1998;539:40-3. PubMed PMID: 10095859.

2: Higa K, Mori M, Shono S, Dan K. Trimetaphan may cause coronary artery spasm. Eur J Anaesthesiol. 1995 Sep;12(5):529-32. PubMed PMID: 8542864.

3: Sha K, Furuya H, Yan S, Kuzumoto N, Furuki T, Okuda T. [Effects of nitroglycerin, prostaglandin E1, trimetaphan and nicardipine on systemic vascular resistance, pulmonary vascular resistance and pulmonary-systemic vascular resistance ratio in dogs]. Masui. 1995 Jul;44(7):944-9. Japanese. PubMed PMID: 7637184.

4: Tsutsui T, Maekawa T, Goodchild C, Jones JG. Cerebral blood flow distribution during induced hypotension with haemorrhage, trimetaphan or nitroprusside in rats. Br J Anaesth. 1995 Jun;74(6):686-90. PubMed PMID: 7640125.

5: Sakata S, Matsumoto Y, Yasumoto S, Abe T, Saito T. [Effects of trimetaphan on hemodynamics and pulmonary gas exchange--a comparison with those of nitroglycerin and prostaglandin E1]. Masui. 1995 Apr;44(4):516-21. Japanese. PubMed PMID: 7776515.

6: Hirata K, Kyushima M, Kawamitsu K, Asato H, Sunagawa H, Uehara H. [A case of torsades de pointes probably caused by trimetaphan intoxication]. J Cardiol. 1994 May-Jun;24(3):243-7. Japanese. PubMed PMID: 8207640.

7: Takasaki M, Sakimura S, Takeshita M, Hamakawa T. [Pharmacokinetics of epidurally administered bupivacaine during prostaglandin E1- or trimetaphan-induced hypotension]. Masui. 1992 May;41(5):779-84. Japanese. PubMed PMID: 1608154.

8: Kitamura A. Circulatory and metabolic changes in the brain during induced hypotension--comparison among trimetaphan, glycerin trinitrate and prostaglandin E1. J Anesth. 1991 Jul;5(3):268-75. PubMed PMID: 15278629.

9: Hirota K, Muraoka M, Takahashi S, Ogasawara E, Ishihara H, Matsuki A. [Effect of induced hypotension with prostaglandin E1 or trimetaphan on endocrine functions in surgical patients]. Masui. 1991 May;40(5):763-8. Japanese. PubMed PMID: 2072520.

10: Ikeda K, Minami Y, Yoshimatsu N, Fujita R, Ikeda T, Isshiki A. [A comparison of induced hypotensive anesthesia using trimetaphan, prostaglandin E1 and nicardipine for neurosurgery]. Masui. 1991 Mar;40(3):400-5. Japanese. PubMed PMID: 2072492.

11: Saitoh N, Mikawa K, Kitamura S, Maekawa N, Goto R, Yaku H, Yamada M, Obara H. Effects of trimetaphan on the cardiovascular response to tracheal intubation. Br J Anaesth. 1991 Mar;66(3):340-4. Erratum in: Br J Anaesth 1992 Feb;68(2):228. PubMed PMID: 2015151.

12: Lloyd-Thomas AR, Cole PV, Prior PF. Isoflurane prevents EEG depression during trimetaphan-induced hypotension in man. Br J Anaesth. 1990 Sep;65(3):313-8. PubMed PMID: 2223359.

13: Takeda S, Inada Y, Tomaru T, Ikeda T, Tashiro N, Morimoto F, Shibata F. [Plasma and red blood cell cyanide concentrations during hypotension induced by sodium nitroprusside or by a nitroprusside-trimetaphan mixture in rabbits]. Masui. 1990 Jun;39(6):701-7. Japanese. PubMed PMID: 2388388.

14: Uno T, Hashida K, Yorozuya Y, Miyako M, Itohda Y. [Blood flow in the operating field during controlled hypotension by nitroglycerin, trimetaphan and prostaglandin E1]. Masui. 1990 Feb;39(2):144-7. Japanese. PubMed PMID: 2109134.

15: Takeda S, Inada Y, Tomaru T, Matsui K, Ikeda T, Morimoto F. [Comparison of effects on carbohydrate metabolism of hypotension induced by sodium nitroprusside and a nitroprusside-trimetaphan mixture in rabbits]. Masui. 1989 Dec;38(12):1605-11. Japanese. PubMed PMID: 2614888.

16: Nam YT, Takahashi S, Tominaga M, Yoshitake J. The hemodynamic and metabolic changes in prostaglandin E1-induced hypotension in dogs--a comparative study with trimetaphan-induced hypotension. J Anesth. 1989 Sep 1;3(2):210-7. PubMed PMID: 15236040.

17: Takeda S, Inada Y, Tomaru T, Kagawa T, Ikeda T, Mozawa N, Morimoto F. [Comparison of endocrine effects of hypotension induced by sodium nitroprusside, trimetaphan camsylate and a nitroprusside-trimetaphan mixture in rabbits]. Masui. 1989 Sep;38(9):1135-41. Japanese. PubMed PMID: 2681862.

18: Swift D. Future unavailability of trimetaphan (Arfonad). Anaesth Intensive Care. 1989 May;17(2):236. PubMed PMID: 2719249.

19: Tanioka F, Ishihara H, Nagao N, Nagao H, Kudoh M, Matsuki A, Oyama T. [Effects of GIK and trimetaphan on glucose metabolism and peripheral circulation]. Masui. 1988 Aug;37(8):933-7. Japanese. PubMed PMID: 3054196.

20: Sury MR, Donaldson MD, Stringer M, Vesey CJ, Cole PV. Cardiovascular actions of trimetaphan nitroprusside. Comparison with sodium nitroprusside in greyhounds. Br J Anaesth. 1988 Jun;60(7):797-802. PubMed PMID: 3395539.