Debrisoquine

Debrisoquine^[1]
Names

IUPAC name 1,2,3,4-tetrahydroisoquinoline-2-carboximidamide
Identifiers
ATC code	C02CC04
CAS Registry Number	1131-64-2^Y
ChEBI	CHEBI:34665^Y
ChEMBL	ChEMBL169901^Y
ChemSpider	2860^Y
DrugBank	DB04840^Y
InChI InChI=1S/C10H13N3/c11-10(12)13-6-5-8-3-1-2-4-9(8)7-13/h1-4H,5-7H2,(H3,11,12)^Y Key: JWPGJSVJDAJRLW-UHFFFAOYSA-N^Y InChI=1/C10H13N3/c11-10(12)13-6-5-8-3-1-2-4-9(8)7-13/h1-4H,5-7H2,(H3,11,12) Key: JWPGJSVJDAJRLW-UHFFFAOYAE
Jmol-3D images	Image
KEGG	C13650^Y
MeSH	Debrisoquine
PubChem	2966
SMILES [N@H]=C(N)N2Cc1c(cccc1)CC2
UNII	X31CDK040E^Y
Properties
Chemical formula	C₁₀H₁₃N₃
Molar mass	175.23032
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Y verify (what is: Y/N?)
Infobox references

Debrisoquine is a derivative of guanidine. It is an antihypertensive drug similar to guanethidine. Debrisoquine is frequently used for phenotyping the CYP2D6 enzyme, a drug metabolizing enzyme.^[2]

Synthesis

Debrisoquin synthesis:^[3] W. Wenner, BE 629007; idem, U.S. Patent 3,157,573 (1963, 1964 both to Hoffmann-La Roche).

References

↑ Debrisoquine - Compound Summary, PubChem.
↑ Fuhr, U.; Jetter, A.; Kirchheiner, J. (2007). "Appropriate Phenotyping Procedures for Drug Metabolizing Enzymes and Transporters in Humans and Their Simultaneous Use in the "Cocktail" Approach". Clinical Pharmacology & Therapeutics 81 (2): 270. doi:10.1038/sj.clpt.6100050.
↑ Wenner, W. (1965). "1,2,3,4-Tetrahydroisoquinoline Derivatives with Antihypertensive Properties". Journal of Medicinal Chemistry 8: 125. doi:10.1021/jm00325a029.

Sympatholytic (and closely related) antihypertensives (C02)

Sympatholytics
(antagonize α-adrenergic
vasoconstriction)

Central

α₂ agonist	Clonidine Guanabenz Guanfacine Methyldopa^#

Adrenergic release inhibitors	Bethanidine Bretylium Debrisoquine Guanadrel Guanazodine Guanethidine Guanoclor Guanazodine Guanoxabenz Guanoxan

Imidazoline receptor agonist	Moxonidine Rilmenidine

Ganglion-blocking/nicotinic antagonist	Mecamylamine Pentolinium Trimethaphan

Peripheral

Indirect

MAOI	Pargyline^‡

Adrenergic uptake inhibitor	Bietaserpine Deserpidine Methoserpidine Rescinnamine Reserpine

Tyrosine hydroxylase inhibitor	Metirosine

Direct

α₁ blockers	Prazosin Indoramin Trimazosin Doxazosin Urapidil

Non-selective α blocker	Phentolamine

Other antagonists

Serotonin antagonist	Ketanserin Lidanserin

Endothelin antagonist (for PH)	dual (Bosentan, Macitentan) selective (Ambrisentan, Sitaxentan)

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

Index of the circulatory system

Description	Anatomy Arteries head and neck arms chest abdomen legs Veins head and neck arms chest abdomen and pelvis legs Development Cells Physiology proteins

Disease	Congenital Neoplasms and cancer Lymphatic vessels Injury Vasculitis Other Symptoms and signs eponymous

Treatment	Procedures Drugs beta blockers channel blockers diuretics nonsympatholytic vasodilatory antihypertensives peripheral vasodilators renin–angiotensin system sympatholytic antihypertensives vasoprotectives

Debrisoquine

Synthesis

See also

References