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Bethanidine

HCID 2368
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Basic informationOverviewNames & identifiersPropertiesChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
55-73-2
Standard SMILES
CN=C(NC)NCc1ccccc1
InChIKey
NIVZHWNOUVJHKV-UHFFFAOYSA-N
Molecular formula
C10H15N3
Average molar mass
177.25 g/mol
Monoisotopic mass
177.12659749

Overview

Bethanidine is a member of guanidines. It has a role as an antihypertensive agent and an adrenergic antagonist.

Names & identifiers

Preferred name
Bethanidine
IUPAC
1-benzyl-2,3-dimethylguanidine
English name
Betanidine
Molecular formula
C10H15N3
Molecular weight
177.25

Names & synonyms

Bethanidine1-BENZYL-2,3-DIMETHYLGUANIDINE55-73-2BetanidinaBetanidinumGuanidine, N,N'-dimethyl-N''-(phenylmethyl)-W8S3YM7AUUN,N'-dimethyl-N''-(phenylmethyl)-guanidineDTXSID7022677CHEBI:37937Bethanidine, Sulfate (2:1)Sulfate, Bethanidine
Show more names
BETANIDINBetanidineBetanidine USP/EP/BPN,N'-Dimethyl-N''-(phenylmethyl)guanidineGuanidine, N,N''-dimethyl-N'-(phenylmethyl)-
RefChem:568014DTXCID3026772-Benzyl-1,3-dimethylguanidineBetanidoleBethanidBatelBenzanidinBenzanidine

Database identifiers

CAS
55-73-2
PubChem CID
2368
DTXSID
DTXSID7022677
ChEMBL
CHEMBL1201260
ChEBI
CHEBI:37937
UNII
W8S3YM7AUU
Nikkaji
J4.563B

Properties

Computed structural properties

XLogP
0.9
Topological polar surface area
36.4 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
1
Rotatable bonds
4
Heavy atoms
13
Formal charge
0
Complexity
160

Experimental & physicochemical properties

DrugsPharmaceuticals -> Listed in ZINC15
LogP0.49
Solubility1.58e+00 g/L
Human DrugsPharmaceuticals
Physical DescriptionSolid

Physicochemical properties

Melting point
195 · 195-197°
Boiling point
299.18 °C · 299.18°C (rough estimate)
Density
0.9826 · 0.9826 (rough estimate)
refractive index
1.48 · 1.4800 (estimate)
pka
10.6 · pKa 10.6 (Uncertain)
FDA UNII
8 S3YM7AUU · W8S3YM7AUU
ATC code
2 CC01 · C02CC01

Chemistry & industry

Pharmacology

Pharmacodynamics · 1 item

Bethanidine is a guanidinium antihypertensive agent that acts by blocking adrenergic transmission. The precise mode of action is not clear. Although bethanidine may produce adverse effects, they are beneficial in severe hypertension and produce fewer side effects than guanethidine.

Mechanism of Action · 1 item

Bethanidine, a guanidine derivative, is a peripherally acting antiadrenergic agent which primarily acts as an alpha2a adrenergic agonist. Bethanidine effectively decreases blood pressure by suppressing renin secretion or interfering with function of the sympathetic nervous system.

Biological Half-Life9 hours (range 7 to 11 hours)
MeSH Pharmacological Classification · 3 items

Drugs used in the treatment of acute or chronic vascular HYPERTENSION regardless of pharmacological mechanism. Among the antihypertensive agents are DIURETICS; (especially DIURETICS, THIAZIDE); ADRENERGIC BETA-ANTAGONISTS; ADRENERGIC ALPHA-ANTAGONISTS; ANGIOTENSIN-CONVERTING ENZYME INHIBITORS; CALCIUM CHANNEL BLOCKERS; GANGLIONIC BLOCKERS; and VASODILATOR AGENTS.

Drugs that inhibit the actions of the sympathetic nervous system by any mechanism. The most common of these are the ADRENERGIC ANTAGONISTS and drugs that deplete norepinephrine or reduce the release of transmitters from adrenergic postganglionic terminals (see ADRENERGIC AGENTS). Drugs that act in the central nervous system to reduce sympathetic activity (e.g., centrally acting alpha-2 adrenergic agonists, see ADRENERGIC ALPHA-AGONISTS) are included here.

Drugs that act on adrenergic receptors or affect the life cycle of adrenergic transmitters. Included here are adrenergic agonists and antagonists and agents that affect the synthesis, storage, uptake, metabolism, or release of adrenergic transmitters.

Absorption, Distribution and ExcretionAbsorbed rapidly in the gastrointestinal tract following oral administration.
Cellular LocationsMembrane

Related reactions

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesChemistry & industryRelated reactionsCompound notes

Uses & manufacturing

Use ClassificationPharmaceuticals

Applications

UsesBetanidine is a betacyanin and an aglycone of the beet dye betanin.

Upstream & downstream products

Upstream raw materials

Methyl carbamimidothioate2-BROMOBENZYLAMINE

Suppliers2 total

陕西缔都医药化工有限公司+86-29-81139210 +86-17392587031 · [email protected]
武汉魔力生物科技有限公司18872289958、027-52304252、3400508168 · [email protected]

Additional notes

DefinitionChEBI: Bethanidine is a member of guanidines. It has a role as an adrenergic antagonist and an antihypertensive agent.