Page 140 - Encyclopedia of Chemical Compounds 3 Vols

H H H H
O
H C C C C C N O
3
H H H H

OTHER NAMES:
Pentyl nitrite
FORMULA:
C 5 H 11 NO 2 or
(CH 3 ) 2 CHCH 2 CH 2 NO 2
Amyl Nitrite
ELEMENTS:
Carbon, hydrogen,
nitrogen, oxygen
COMPOUND TYPE:
OVERVIEW
Ester (organic) KE
Amyl nitrite (A-mil NYE-trite) commonly occurs in two
STATE: Y
Liquid isomeric forms: n-amyl nitrite and isoamyl nitrite (3-methy-
lamyl nitrite or 3-methylpentyl nitrite). In common usage,
MOLECULAR WEIGHT: F
the term amyl nitrite most commonly refers to the isoamyl
117.15 g/mol A
form. Both isomers occur as yellowish liquids with a distinc-
MELTING POINT: C tive sweet odor and a pungent taste. They are unstable and
Not available T break down when exposed to air, light, or water. Both iso-
mers are probably best known as vasodilators, substances
BOILING POINT:
S
that cause blood vessels to relax and expand, allowing an
n-amyl nitrite: 104.5 C

(220 F); isoamyl increased flow of blood through the body. Because of its

nitrite: 99.2 C (210 F) widespread use as a hazardous recreational drug, isoamyl
nitrite has been banned, except for specified medical uses.
SOLUBILITY:
Almost insoluble in
water; soluble in
HOW IT IS MADE
alcohol
Isoamyl nitrite is prepared in a straightforward synthesis
in the reaction between isoamyl alcohol (CH 3 ) 2 CHCH 2 CH 2 OH)
and nitrous acid (HNO 2 ). The usual method of preparation is
CHEMICAL COMPOUNDS 89