TRIMETHAPHAN

Details

Stereochemistry	MIXED
Molecular Formula	C22H25N2OS
Molecular Weight	365.512
Optical Activity	UNSPECIFIED
Defined Stereocenters	0 / 4
E/Z Centers	0
Charge	1

SHOW SMILES / InChI

Structure Search

SMILES

O=C1N(CC2=CC=CC=C2)C3C[S+]4CCCC4C3N1CC5=CC=CC=C5

InChI

InChIKey=CHQOEHPMXSHGCL-UHFFFAOYSA-N

InChI=1S/C22H25N2OS/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/h1-6,8-11,19-21H,7,12-16H2/q+1

HIDE SMILES / InChI

Molecular Formula	C22H25N2OS
Molecular Weight	365.512
Charge	1
Count

Stereochemistry	MIXED
Additional Stereochemistry	No
Defined Stereocenters	0 / 4
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.drugs.com/mmx/trimethaphan-camsylate.html | https://www.ncbi.nlm.nih.gov/pubmed/8618259

Trimethaphan (or Trimethaphan camsylate), a ganglionic blocking agent and an antihypertensive drug, was marketed under the brand name Arfonad. Arfonad is indicated to induce systemic arterial hypotension in patients undergoing major surgery and to treat severe systemic hypertension, and in the emergency treatment of pulmonary edema in patients with pulmonary hypertension associated with systemic hypertension. Trimethaphan prevents stimulation of postsynaptic receptors by competing with acetylcholine for these receptor sites. Additional effects may include direct peripheral vasodilation and release of histamine. This drug was discontinued because of the competition from newer drugs that are more selective in their actions and effects.

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Hypertension 575 Sources: https://www.accessdata.fda.gov/scripts/cder/daf/index.cfm?event=overview.process&ApplNo=008983	Primary		Approved 8583	ARFONAD Approved Use Hypotension, controlled (induction and maintenance) - Trimethaphan is indicated for production of controlled hypotension during surgery to reduce bleeding into the surgical field. Hypertension (treatment) - Trimethaphan is indicated for rapid reduction of blood pressure in the treatment of hypertensive emergencies, especially in patients with acute dissecting aneurysm, and in the emergency treatment of pulmonary edema in patients with pulmonary hypertension associated with systemic hypertension.

Doses

Dose	Population	Adverse events
9 mg/min 1 times / day multiple, intravenous Studied dose Dose: 9 mg/min, 1 times / day Route: intravenous Route: multiple Dose: 9 mg/min, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/938175/	unhealthy, 23 to 66 years Health Status: unhealthy Age Group: 23 to 66 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/938175/	Disc. AE: Respiratory arrest... AEs leading to discontinuation/dose reduction: Respiratory arrest Sources: https://pubmed.ncbi.nlm.nih.gov/938175/
0.115 mg/kg 1 times / day single, intravenous Studied dose Dose: 0.115 mg/kg, 1 times / day Route: intravenous Route: single Dose: 0.115 mg/kg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/13059864/	pregnant, adult Health Status: pregnant Age Group: adult Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/13059864/	Other AEs: Yawning, Sensation of warmth... Other AEs: Yawning Sensation of warmth Nausea Vomiting Pallor Dizziness Sources: https://pubmed.ncbi.nlm.nih.gov/13059864/

AEs

AE	Significance	Dose	Population
Respiratory arrest	Disc. AE	9 mg/min 1 times / day multiple, intravenous Studied dose Dose: 9 mg/min, 1 times / day Route: intravenous Route: multiple Dose: 9 mg/min, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/938175/	unhealthy, 23 to 66 years Health Status: unhealthy Age Group: 23 to 66 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/938175/
Dizziness		0.115 mg/kg 1 times / day single, intravenous Studied dose Dose: 0.115 mg/kg, 1 times / day Route: intravenous Route: single Dose: 0.115 mg/kg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/13059864/	pregnant, adult Health Status: pregnant Age Group: adult Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/13059864/
Nausea		0.115 mg/kg 1 times / day single, intravenous Studied dose Dose: 0.115 mg/kg, 1 times / day Route: intravenous Route: single Dose: 0.115 mg/kg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/13059864/	pregnant, adult Health Status: pregnant Age Group: adult Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/13059864/
Pallor		0.115 mg/kg 1 times / day single, intravenous Studied dose Dose: 0.115 mg/kg, 1 times / day Route: intravenous Route: single Dose: 0.115 mg/kg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/13059864/	pregnant, adult Health Status: pregnant Age Group: adult Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/13059864/
Sensation of warmth		0.115 mg/kg 1 times / day single, intravenous Studied dose Dose: 0.115 mg/kg, 1 times / day Route: intravenous Route: single Dose: 0.115 mg/kg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/13059864/	pregnant, adult Health Status: pregnant Age Group: adult Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/13059864/
Vomiting		0.115 mg/kg 1 times / day single, intravenous Studied dose Dose: 0.115 mg/kg, 1 times / day Route: intravenous Route: single Dose: 0.115 mg/kg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/13059864/	pregnant, adult Health Status: pregnant Age Group: adult Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/13059864/
Yawning		0.115 mg/kg 1 times / day single, intravenous Studied dose Dose: 0.115 mg/kg, 1 times / day Route: intravenous Route: single Dose: 0.115 mg/kg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/13059864/	pregnant, adult Health Status: pregnant Age Group: adult Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/13059864/

Sourcing

Vendor/Aggregator	ID	URL
ABI Chem	AC1L2MN5
ABI Chem	AC1Q6LI1
Alfa Chemistry	ACM68917
BOC Sciences	21035-85-8
BOC Sciences	68-91-7
BOC Sciences	7187-66-8
ChemMol	99147727	http://www.chemmol.com/chemmol/99147727.html
Compound Cloud	23576
Compound Cloud	441310
eMolecules	110042105
eMolecules	313119497
eNovation Chemicals	D673675	https://www.enovationchem.com/ProductDetails.asp?ProductID=D673675
MuseChem	I009884
MuseChem	M019330
Tetrahedron	TS74953
THE BioTek	bt-425772	https://www.thebiotek.com/product/others/bt-425772
Toronto Research Chemicals	T344755
Toronto Research Chemicals	T795435
ZINC	ZINC000003831581	http://zinc15.docking.org/substances/ZINC000003831581
ZINC	ZINC000003938748	http://zinc15.docking.org/substances/ZINC000003938748
ZINC	ZINC000100308855	http://zinc15.docking.org/substances/ZINC000100308855
ZINC	ZINC000100308860	http://zinc15.docking.org/substances/ZINC000100308860
ZINC	ZINC000207869944	http://zinc15.docking.org/substances/ZINC000207869944

PubMed

Title	Date	PubMed
Role of the multidomain protein spinophilin in blood pressure and cardiac function regulation.	2008-10	18711009
Cerebral blood-flow responses to induced hypotension and to CO2 inhalation in patients with major cerebral artery occlusive disease: a positron-emission tomography study.	1999-02	10090598
Effects of trimetaphan-induced deliberate hypotension on human cochlear blood flow.	1998	10095859
Differential microcirculation dynamics during deliberate hypotension induced by nicardipine, PGE1 and trimethaphan in rat mesentery.	1995-11	8590494
Trimetaphan may cause coronary artery spasm.	1995-09	8542864
Cerebral blood flow distribution during induced hypotension with haemorrhage, trimetaphan or nitroprusside in rats.	1995-06	7640125
[Effect of deliberate hypotension on renal functions during epidural block plus inhalation anesthesia: a comparison of prostaglandin E1 and trimethaphan].	1994-10	7815696
Epidural blood flow during prostaglandin E1 or trimethaphan induced hypotension.	1994-04	8022855
Epidural blood flow during prostaglandin E1 or trimethaphan induced hypotension.	1993-11	8302922
Effects of ischemia duration on neurological outcome, CA1 histopathology, and nonmatching to sample learning in monkeys.	1992-10	1412584
[Pharmacokinetics of epidurally administered bupivacaine during prostaglandin E1- or trimetaphan-induced hypotension].	1992-05	1608154
Chronic lesion of rostral ventrolateral medulla in spontaneously hypertensive rats.	1992-02	1735570
[Effects of induced hypotensive anesthesia on the blood coagulation-fibrinolysis system measured by thrombelastography--comparison between prostaglandin E1 and trimethaphan].	1992-01	1545507
[Baroreceptor reflex response to acute blood loss during induced hypotension--a comparison of sodium nitroprusside, prostaglandin E1 and trimethaphan].	1990-05	2384952
The hemodynamic and metabolic changes in prostaglandin E1-induced hypotension in dogs--a comparative study with trimetaphan-induced hypotension.	1989-09-01	15236040
Acute left bundle branch block precipitated by trimethaphan.	1989-09	2774249
[Difference in susceptibility between auditory and equilibrium function in rabbits with experimentally-induced transient ischemic attack].	1989-02	2746423
The effect of trimethaphan-induced hypotension on canine spinal cord blood flow. Measurement at different cord levels using radiolabelled microspheres.	1988-05	3187693
[Effect of trimethaphan-induced hypotension on carbohydrate metabolism].	1986-10	3543428
The influence of trimethaphan (Arfonad)-induced hypotension with and without spine distraction on canine spinal cord blood flow.	1986-04	3715622
[Effect of trimethaphan-induced hypotension on pituitary-adrenocortical function].	1986-03	3012136
Regional blood flows during induced hypotension produced by nitroprusside or trimethaphan in the rhesus monkey.	1985-08	4014741
Hemodynamics and myocardial metabolism under deliberate hypotension. An experimental study in dogs.	1983-12	6673474
Changes in cardiac output and systemic arterial pressure after insertion of acrylic cement during trimetaphan, sodium nitroprusside and glycerol trinitrate-induced hypotension. A comparison with changes during normotension.	1983-08	6411105
[Effect of hypotension induced by trimethaphan and nitroglycerin on intraocular pressure in man].	1983-02	6406719
Profound arterial hypotension in dogs: brain electrical activity and organ integrity.	1983-01	6848019
Cerebral and systemic effects of hypotension induced by trimetaphan or nitroprusside in dogs.	1982-12	7158277
Trimethaphan-induced hypotension: effect on renal function.	1982-11	7139398
Altered osmotic threshold for vasopressin release and impaired thirst sensation: additional abnormalities in Kallmann's syndrome.	1982-10	7107821
Autoregulation of myocardial blood flow under controlled hypotension in the dog.	1982-06	7113627
[The effects of controlled hypotension induced by prostaglandin E1 and trimethaphan on coronary and systemic hemodynamics and myocardial contractility (author's transl)].	1982-04	7202062
[A comparison of the metabolic effects of hypotension induced by arteriotomy, trimethaphan, nitroprusside, or deep halothane in dog (author's transl)].	1981-09	7328742
Brain blood flow and metabolism after global ischemia and post-insult thiopental therapy in monkeys.	1979-09-01	116395
Postischemic brain oxygenation with barbiturate therapy in rats.	1979-08	37043
Cerebral energy levels during trimethaphan-induced hypotension in the rat: effects of light versus deep halothane anesthesia.	1979-01	760601
[Use of methoxamine in trimethaphan-induced hypotension].	1979-01	424896
Prolonged apnea following trimethaphan and succinylcholine.	1979-01	216287
[Electrocardiographic changes observed during the use of trimethaphan in the treatment of malignant arterial hypertension].	1978-08	727981
Selective osmoreceptor dysfunction in the syndrome of chronic hypernatremia.	1977-04	849975
Canine systemic and cerebral effects of hypotension induced by hemorrhage, trimethaphan, halothane, or nitroprusside.	1977-03	842872
Pyramidal tract responses (PTR) during hypoxia and hypotension.	1976-09-01	960174
[The effects of sodiumnitroprusside and trimethaphan induced hypotension on haemodynamics and myocardial oxygen consumption (author's transl)].	1976-01	1259127

Patents

Sample Use Guides

In Vivo Use Guide

Controlled hypotension during surgery: Initial: Intravenous infusion, 3 to 4 mg per minute, adjusted according to response. Maintenance: Intravenous infusion, 300 mcg (0.3 mg) to 6 mg per minute. Hypertensive emergency: Initial: Intravenous infusion, 500 mcg (0.5 mg) to 1 mg per minute, adjusted according to response. Maintenance: Intravenous infusion, 1 to 5 mg per minut

Route of Administration: Intravenous

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:25:14 GMT 2025` Edited by `admin` on `Mon Mar 31 18:25:14 GMT 2025`
Record UNII	6G8X656T45
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

TRIMETAPHAN

Preferred Name

English

TRIMETHAPHAN

Common Name

English

THIENO(1',2':1,2)THIENO(3,4-D)IMIDAZOLIUM, DECAHYDRO-2-OXO-1,3-BIS(PHENYLMETHYL)-

Systematic Name

English

TRIMETHAPHAN CATION

Common Name

English

TRIMETHAPHAN ION

Common Name

English

Trimetaphan [WHO-DD]

Common Name

English

1,3-DIBENZYL-2-OXODECAHYDROTHIENO(1',2':1,2)THIENO(3,4-D)IMIDAZOL-5-IUM

Systematic Name

English

Classification Tree Code System Code

WHO-VATC

QC02BA01