DDAIP

DDAIP
Clinical data
Other names	Dodecyl 2-N,N-dimethylaminopropionate; Dodecyl-2-(dimethylamino)propionate; N,N-Dimethylalanine dodecyl ester
Pharmacokinetic data
Bioavailability	<1% (topical)
Protein binding	>99%
Metabolism	Esterase mediated
Elimination half-life	5 hours
Excretion	Urinary
Identifiers
	IUPAC name 2-Dimethylaminopropionic acid dodecyl ester (Decyl (C10) ester shown);
CAS Number	149196-89-4 ;
PubChem CID	3025823;
ChemSpider	2291478;
UNII	6679UF28DO;
CompTox Dashboard (EPA)	DTXSID70933573 ;
Chemical and physical data
Formula	C17H36ClNO2
Molar mass	321.93 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCCCCCCCCCCCOC(=O)C(C)N(C)C;
	InChI InChI=1S/C17H35NO2/c1-5-6-7-8-9-10-11-12-13-14-15-20-17(19)16(2)18(3)4/h16H,5-15H2,1-4H3; Key:HSMMSDWNEJLVRY-UHFFFAOYSA-N;
	(verify)

DDAIP is a pharmaceutical ingredient added to topical products to increase penetration through the skin. Chemically, DDAIP is an ester of N,N-dimethylalanine and dodecanol, although as of now the structural formula shows an ester with decanol (C10) instead. DDAIP is typically formulated as its hydrochloride salt (DDAIP.HCl). This salt is a white crystalline solid with a melting range of 88-93 °C and is an amphiphilic molecule with a pKa of 4.87 that is soluble in water up to about 40% w/v. DDAIP is proprietary to NexMed USA, a subsidiary of Apricus Biosciences.^[1]

^ US 6118020, Buyuktimkin S, Buyuktimkin N, "Crystalline salts of dodecyl 2-(N,N-dimethylamino)-propionate", issued 12 September 2000, assigned to Nexmed Holdings Inc

[Patent-1] US 6118020, Buyuktimkin S, Buyuktimkin N, "Crystalline salts of dodecyl 2-(N,N-dimethylamino)-propionate", issued 12 September 2000, assigned to Nexmed Holdings Inc

[1]