Bromazine

Not to be confused with Promazine.

Bromazine, sold under the brand names Ambodryl, Ambrodil, and Deserol among others, also known as bromodiphenhydramine, is an antihistamine and anticholinergic medication of the ethanolamine class.^{[1][2][3][4][5]} It is an analogue of diphenhydramine with a bromine substitution on one of the phenyl rings.^[1][2]

Bromazine

Clinical data
Trade names	Ambodryl, Ambrodil, Deserol
Other names	Bromodiphenhydramine; Bromdiphenhydramine
MedlinePlus	a682065
Routes of administration	Oral
ATC code	R06AA01 (WHO)
Pharmacokinetic data
Bioavailability	High
Protein binding	96%
Metabolism	Mostly hepatic (CYP-mediated), also renal
Elimination half-life	1 to 4 hours
Identifiers
IUPAC name 2-[(4-Bromophenyl)-phenylmethoxy]-N,N-dimethylethanamine
CAS Number	1808-12-4 Y 1808-12-4
PubChem CID	2444
IUPHAR/BPS	7132
DrugBank	DB01237 Y
ChemSpider	2350 Y
UNII	202J683U97
ChEBI	CHEBI:59177 Y
ChEMBL	ChEMBL1201245 N
CompTox Dashboard (EPA)	DTXSID6022688
ECHA InfoCard	100.003.854
Chemical and physical data
Formula	C17H20BrNO
Molar mass	334.257 g·mol−1
3D model (JSmol)	Interactive image
SMILES Brc1ccc(cc1)C(OCCN(C)C)c2ccccc2
InChI InChI=1S/C17H20BrNO/c1-19(2)12-13-20-17(14-6-4-3-5-7-14)15-8-10-16(18)11-9-15/h3-11,17H,12-13H2,1-2H3 Y Key:NUNIWXHYABYXKF-UHFFFAOYSA-N Y
NY (what is this?)  (verify)

Synthesis

Synthesis:^[6] Patent:^[7]

Grignard reaction between phenylmagnesium bromide and para-bromobenzaldehyde [1122-91-4] (1) gives p-bromobenzhydrol [29334-16-5] (2). Halogenation with acetyl bromide in benzene solvent gives p-bromo-benzhydrylbromide [18066-89-2] (3). Finally, etherification with deanol completed the synthesis of Bromazine (4).

Side effects

Continuous and/or cumulative use of anticholinergic medications, including first-generation antihistamines, is associated with higher risk for cognitive decline and dementia in elderly people.^[8][9]