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7 Medicinal chemistry
the N has four bonds and so is permanently charged. The non-depolarizing
muscle relaxants have quaternary nitrogens (e.g. vecuronium, atracurium).
Benzyl:This group has an unsaturated (i.e. contains some double C=Cbonds)
6-carbon ring structure; benzene has the formula C 6 H 6 .Ithas a planar ring
structure and is a solvent for lipids but is not water-soluble. It is a common group
in drug molecules, for example, etomidate, and often substituted with a halogen
as in ketamine (chlorine) and some benzodiazepines (chlorine).
Carbamyl:The group−CONH 2 .The dimethyl derivative of this group is present
and ester-linked in some of the anticholinesterase inhibitors, such as
neostigmine (hence a carbamate ester). As a result of enzyme interaction the
enzyme becomes carbamylated instead of acetylated with slower recovery of the
esteratic site.
Carboxylic acid:Generic term for acids derived from alkanols. The first two
members of the series have special names: formic acid and acetic acid from
methanol and ethanol. The others are named according to the alkanol, for
example, propionic acid from n-propanol. Acids, therefore proton donors and
water soluble.
Catechol:1,2-hydroxybenzene. Both−OH groups are required before a compound
can be metabolized by COMT (catechol O-methyltransferase) when the−OH
group is methylated to−OCH 3 .Innoradrenaline, the main substituent on the
benzyl ring is the ethylamine group, which is therefore numbered 1, so the two
−OH groups are renumbered as 3 and 4.