Space filling model of<unk> .<unk>  is also known as β-hydroxyamphetamine, and is a member of the phenethylamine and amphetamine chemical classes. It is closely related to the cathinones (β-ketoamphetamines). The compound exists as four stereoisomers, which include d- and l-norephedrine and d- and l-norpseudoephedrine. d-Norpseudoephedrine is also known as cathine, and is found naturally in Catha edulis (khat). Pharmaceutical drug preparations of<unk>  have varied in their stereoisomer composition in different countries, which may explain differences in misuse and side effect profiles. Analogues of<unk>  include ephedrine, pseudoephedrine, amphetamine, methamphetamine, and cathinone.<unk> , structurally, is in the substituted phenethylamine class, consisting of a cyclic benzene or phenyl group, a two carbon ethyl moiety, and a terminal nitrogen, hence the name phen-ethyl-amine. The methyl group on the alpha carbon (the first carbon before the nitrogen group) also makes this compound a member of the substituted amphetamine class. Ephedrine is the N-methyl analogue of<unk> . Exogenous compounds in this family are degraded too rapidly by monoamine oxidase to be active at all but the highest doses. However, the addition of the α-methyl group allows the compound to avoid metabolism and confer an effect. In general, N-methylation of primary amines increases their potency; whereas β-hydroxylation decreases CNS activity, but conveys more selectivity for adrenergic receptors.
Phenylpropanolamine
Ergine
Cromoglicic acid
Tetrahydropapaveroline
Methylenedioxypyrovalerone
Azacyclonol
Papaverine
Cannabidiol