Dopastin

Dopastin
Names

Systematic IUPAC name (2E)-N-{(2S)-2-[Hydroxy(nitroso)amino]-3-methylbutyl}-2-butenamide
Identifiers
CAS Number	37134-80-8
3D model (Jmol)	Interactive image
ChemSpider	4939169
PubChem	6434226
InChI InChI=1S/C9H17N3O3/c1-4-5-9(13)10-6-8(7(2)3)12(15)11-14/h4-5,7-8,15H,6H2,1-3H3,(H,10,13)/b5-4+/t8-/m1/s1 Key: FJUBKTNNXRFHFD-WTSVBCDHSA-N InChI=1/C9H17N3O3/c1-4-5-9(13)10-6-8(7(2)3)12(15)11-14/h4-5,7-8,15H,6H2,1-3H3,(H,10,13)/b5-4+/t8-/m1/s1 Key: FJUBKTNNXRFHFD-WTSVBCDHBR
SMILES O=C(NC[C@@H](N(O)N=O)C(C)C)/C=C/C
Properties
Chemical formula	C₉H₁₇N₃O₃
Molar mass	215.25 g·mol⁻¹
Melting point	116 to 119 °C (241 to 246 °F; 389 to 392 K)^[1]
Acidity (pK_a)	5.1^[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Dopastin is a chemical compound produced by the bacteria Pseudomonas No. BAC-125.^[2] It was first isolated and characterized in 1972. It is an inhibitor of the enzyme dopamine β-hydroxylase.^[3]

Dopastin can be prepared synthetically from L-valinol.^[4]

References

1 2 Merck Index, 11th Edition, 3417
↑ Iimura, H; Takeuchi, T; Kondo, S; Matsuzaki, M; Umezawa, H (1972). "Dopastin, an inhibitor of dopamine -hydroxylase". The Journal of antibiotics. 25 (8): 497–500. doi:10.7164/antibiotics.25.497. PMID 4648494.
↑ H. Iinuma; M. Matsuzaki; T. Nagatsu; T. Takeuchi; H. Umezawa (1974). "Biochemical and biological studies on dopastin, an inhibitor of dopamine β-hydroxylase". Agric. Biol. Chem. 38 (11): 2107–2111. doi:10.1271/bbb1961.38.2107.
↑ Ohno, M.; Iinuma, H.; Yagisawa, N.; Shibahara, S.; Suhara, Y.; Kondo, S.; Maeda, K.; Umezawa, H. (1973). "Synthesis of dopastin, a dopamine ?-hydroxylase inhibitor of microbial origin". Journal of the Chemical Society, Chemical Communications (4): 147. doi:10.1039/C39730000147.

Monoamine metabolism modulators

Common
(non-specific)

AAAD

MAO

Inhibitors: Non-selective: Benmoxin Caroxazone Echinopsidine Furazolidone Guineesine Hydralazine Indantadol Iproclozide Iproniazid Isocarboxazid Isoniazid Linezolid Mebanazine Metfendrazine Nialamide Octamoxin Paraxazone Phenelzine Pheniprazine Phenoxypropazine Pivhydrazine Procarbazine Safrazine Tranylcypromine

Inhibitors: MAO-A-selective: Amiflamine Bazinaprine Befloxatone Brofaromine Cimoxatone Clorgiline CX157 (Tyrima) Eprobemide Esuprone Harmala alkaloids (e.g., harmine, harmaline, harman, norharman, tetrahydroharmine) Methylene blue Metralindole Minaprine Moclobemide Pirlindole Sercloremine Tetrindole Toloxatone

Inhibitors: MAO-B selective: Almoxatone D-Deprenyl Ethanol Ladostigil Lazabemide Milacemide Mofegiline Nicotine Pargyline^‡ Rasagiline Safinamide Selegiline (L-Deprenyl)

Phenethylamines
(dopamine, epinephrine,
norepinephrine)

PAH	Inhibitors: 3,4-Dihydroxystyrene

TH	Inhibitors: 2-Hydroxyestradiol 2-Hydroxyestrone 3-Iodotyrosine Aquayamycin Bulbocapnine Metirosine Oudenone

DBH	Inhibitors: Bupicomide Disulfiram Dopastin Fusaric acid Nepicastat Phenopicolinic acid Tropolone

PNMT	Inhibitors: CGS-19281A SKF-64139 SKF-7698

COMT	Inhibitors: 2-Hydroxyestradiol 2-Hydroxyestrone Entacapone Nitecapone Tolcapone

Tryptamines
(serotonin, melatonin)

TPH	Inhibitors: AGN-2979 Fenclonine (PCPA) Telotristat

See also: Adrenergics • Dopaminergics • Melatonergics • Serotonergics • Monoamine reuptake and release modulators • Monoamine neurotoxins

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