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Debrisoquine

HCID 2966
NotesReactions

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Basic informationNames & identifiersPropertiesChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
1131-64-2
Standard SMILES
N=C(N)N1CCc2ccccc2C1
InChIKey
JWPGJSVJDAJRLW-UHFFFAOYSA-N
Molecular formula
C10H13N3
Average molar mass
175.23 g/mol
Monoisotopic mass
175.11094743

Names & identifiers

Preferred name
Debrisoquine
IUPAC
3,4-dihydro-1H-isoquinoline-2-carboximidamide
English name
debrisoquine
Molecular formula
C10H13N3
Molecular weight
175.23

Names & synonyms

DebrisoquineDebrisoquin1131-64-2DebrisochinumDebrisoquinaDebrisoquinum2(1H)-Isoquinolinecarboximidamide, 3,4-dihydro-1,2,3,4-tetrahydroisoquinoline-2-carboximidamide3,4-dihydro-1H-isoquinoline-2-carboximidamideX31CDK040EDTXSID7022885CHEBI:34665
Show more names
ebrisoquinDebrisochinDebrisoquine Monomer3,4-Dihydro-2(1H)-isoquinolinecarbimidamide3,4-DIHYDRO-1H-ISOQUINOLINE-2-CARBOXAMIDINE3,4-Dihydro-2(1H)-isoquinolinecarboximidamide
RefChem:388913DTXCID202885C02CC04214-470-1IsocaramidineTendor3,4-dihydroisoquinoline-2(1H)-carboximidamide3,4-Dihydro-2(1H)-isoquinolinecarboxamidine

Database identifiers

CAS
1131-64-2
PubChem CID
2966
DTXSID
DTXSID7022885
ChEMBL
CHEMBL169901
ChEBI
CHEBI:34665
UNII
X31CDK040E
EC Number
214-470-1
Nikkaji
J7.269I

Properties

Computed structural propertiesFilling in

XLogP
0.8
Topological polar surface area
53.1 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
1
Rotatable bonds
1
Heavy atoms
13
Formal charge
0
Complexity
202

Experimental & physicochemical properties

LogP · 2 items

0.75

0.75

Melting Point · 2 items

278-280 °C

278 - 280 °C

Physical DescriptionSolid

Physicochemical properties

Melting point
278 · 278-280 °C
Boiling point
309.8 · 309.8±52.0 °C(Predicted)
Density
1.24 · 1.24±0.1 g/cm3(Predicted)
pka
11.9 · pKa 11.9 (Uncertain)
FDA UNII
31 CDK040E · X31CDK040E
ATC code
2 CC04 · C02CC04

Chemistry & industry

Pharmacology

ATC Code · 2 items

C - Cardiovascular system;C02 - Antihypertensives;C02C - Antiadrenergic agents, peripherally acting;C02CC - Guanidine derivatives;C02CC04 - Debrisoquine

QC - Cardiovascular system;QC02 - Antihypertensives;QC02C - Antiadrenergic agents, peripherally acting;QC02CC - Guanidine derivatives;QC02CC04 - Debrisoquine

Pharmacodynamics · 1 item

Debrisoquin is an adrenergic neuron-blocking drug similar in effects to guanethidine. It is a substrate for a polymorphic cytochrome P-450 enzyme. Persons with certain isoforms of this enzyme are unable to properly metabolize this and many other clinically important drugs. They are commonly referred to as having a debrisoquin 4-hydroxylase polymorphism.

Mechanism of Action · 1 item

Debrisoquin acts at the sympathetic neuroeffector junction by inhibiting or interfering with the release and/or distribution of norepinephrine, rather than acting at the effector cell by inhibiting the association of norepinephrine with its receptors. It is taken up by norepinephrine transporters. It becomes concentrated in NE transmitter vesicles, replacing NE in these vesicles. This leads to a gradual depletion of NE stores in the nerve endings. Once inside the terminal it blocks the release of noradrenaline in response to arrival of an action potential. In contrast to ganglionic blocking agents, debrisoquin suppresses equally the responses mediated by alpha-and beta-adrenergic receptors but does not produce parasympathetic blockade. Since sympathetic blockade results in modest decreases in peripheral resistance and cardiac output, debrisoquin lowers blood pressure in the supine position. It further reduces blood pressure by decreasing the degree of vasoconstriction that normally results from reflex sympathetic nervous activity upon assumption of the upright posture, thus reducing venous return and cardiac output more.

Metabolism/Metabolites · 2 items

Hepatic.

Debrisoquine has known human metabolites that include 4-Hydroxydebrisoquine.

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.

Related reactions

2 records
New reaction record
HRID 542286 reaction equation
HRID 542286As productuspto-grants-1987_04
HRID 2231166 reaction equation
HRID 2231166As productuspto-grants-1988_11

Compound notes

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On this pageBasic informationNames & identifiersPropertiesChemistry & industryRelated reactionsCompound notes

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.

Cellular LocationsCytoplasm;Extracellular

Applications

UsesAntihypertensive.

Upstream & downstream products

Upstream raw materials

7-Methoxy-1,2,3,4-tetrahydro-isoquinoline hydrochloride

Suppliers13 total

Syntechem Co.,Ltd[email protected]
湖北扬信医药科技有限公司15347293736 · [email protected]
BOC Sciences16314854226; +8616314854226 · [email protected]
陕西缔都医药化工有限公司029-029-81120477 17792793610 · [email protected]
上海陶术生物科技股份有限公司13564774135 · [email protected]
河北贞佳新材料有限公司0319-5925599 13315915972 · [email protected]
湖北扬信医药科技有限公司15374522761 · [email protected]
华阴市赛普生物科技有限公司13892502238 · [email protected]
湖北信康医药化工有限公司027-027-59308705 18871579363 · [email protected]
TargetMol中国(陶术生物)4008200310 15002144251 · [email protected]
DAYANG CHEM (HANGZHOU) CO.,LTD+86-88938639 +86-17705817739 · [email protected]
Shaanxi Dideu Medichem Co. Ltd+86-17392712779 · [email protected]
南京世洲生物科技有限公司025-85563444 15850508050 · [email protected]

Additional notes

DefinitionChEBI: Debrisoquin is a member of isoquinolines and a carboxamidine. It has a role as an antihypertensive agent, an adrenergic agent, a sympatholytic agent and a human metabolite.