Butalamine

Butalamine
Clinical data
ATC code	C04AX23 (WHO) ;
Identifiers
	IUPAC name N,N-Dibutyl-N'-(3-phenyl-1,2,4-oxadiazol-5-yl)ethane-1,2-diamine;
CAS Number	22131-35-7;
PubChem CID	30949;
ChemSpider	28712;
UNII	140T9JTG43;
ChEMBL	ChEMBL1697825;
CompTox Dashboard (EPA)	DTXSID1022710 ;
ECHA InfoCard	100.040.708
Chemical and physical data
Formula	C18H28N4O
Molar mass	316.449 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES n1c(onc1c2ccccc2)NCCN(CCCC)CCCC;

Butalamine is a vasodilator.^[1]

Synthesis

Check with imolamine (alternate nitrogen reacts)

USA Ex 9: The halogenation of benzamidoxime (1) with chlorine and subsequent reaction with cyanamide (3) gives 5-amino-3-phenyl-1,2,4-oxadiazole (4). Base catalyzed alkylation with dibutylaminoethyl chloride (5) completes the synthesis of butalamine (6).

References

^ Sterne J (April 1976). "". Fortschritte Der Medizin (in German). 94 (11): 657–9. PMID 823083.
^ Aron-samuel Jan Marcel Didier, FR3334M (1965 to Jan Marcel).
^ Japan. Pat., 76 108 068, (1976); CA, 87, 5981b
^ Aron-Samuel Jan Marcel Didier, Sterne Jean Jacques, U.S. patent 3,338,899 (1967 to).

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[Sterne_1976-1] Sterne J (April 1976). "". Fortschritte Der Medizin (in German). 94 (11): 657–9. PMID 823083.

[2] Aron-samuel Jan Marcel Didier, FR3334M (1965 to Jan Marcel).

[3] Japan. Pat., 76 108 068, (1976); CA, 87, 5981b

[4] Aron-Samuel Jan Marcel Didier, Sterne Jean Jacques, U.S. patent 3,338,899 (1967 to).

[1]

[2]

[3]

[4]

v t e Peripheral vasodilators (C04)
Phenylethanolamine derivatives	Isoxsuprine Buphenine Bamethan
Alpha blockers	Non-selective Buflomedil Phentolamine Phenoxybenzamine Tolazoline Selective α₁-blockers Alfuzosin Doxazosin Prazosin Silodosin Tamsulosin Terazosin
Niacin and derivatives	Niacin Nicotinyl alcohol Inositol nicotinate Ciclonicate
Purine derivatives	Pentifylline Xantinol nicotinate Pentoxifylline Etofylline nicotinate
Ergot alkaloids	Ergoloid Nicergoline Dihydroergocristine
Other peripheral vasodilators	Cyclandelate Vincamine Moxisylyte Bencyclane Vinburnine Sulcotidil Naftidrofuryl Butalamine Visnadine Cetiedil Cinepazide Ifenprodil Azapetine Fasudil

Clinical data

ATC code	C04AX23 (WHO)
Identifiers
IUPAC name N,N-Dibutyl-N'-(3-phenyl-1,2,4-oxadiazol-5-yl)ethane-1,2-diamine
CAS Number	22131-35-7
PubChem CID	30949
ChemSpider	28712
UNII	140T9JTG43
ChEMBL	ChEMBL1697825
CompTox Dashboard (EPA)	DTXSID1022710
ECHA InfoCard	100.040.708
Chemical and physical data
Formula	C₁₈H₂₈N₄O
Molar mass	316.449 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES n1c(onc1c2ccccc2)NCCN(CCCC)CCCC