8082. 3-Quinuclidinol

Nomenclature

CAS number: 1619-34-7
1-Azabicyclo[2.2.2]octan-3-ol; 3-hydroxyquinuclidine.
C7H13NO; mol wt 127.18.
C 66.11%, H 10.30%, N 11.01%, O 12.58%.

Description and references

Prepn and resolution of dl-forms: Sternbach, Kaiser, J. Am. Chem. Soc. 74, 2215 (1952); Sternbach, US 2648667 (1953 to Hoffmann-La Roche); of free alcohol, acetate and/or benzoate esters: Grob et al., Helv. Chim. Acta 40, 2170 (1957); Mikhalina, Rubtsov, Zh. Obshch. Khim. 30, 163 (1960), C.A. 54, 22632h (1960). Structure activity of esters: M. D. Mashkovsky in Proc. 1st Int. Pharmacol. Mtg. Stockholm, 1961 vol. 7 (Macmillan, NewYork, 1963) pp 359-366.

Chemical structure

Derivative

dl-Form.

Nomenclature

CAS number: 3684-26-2

Properties

Crystals from benzene or acetone, mp 221-223° also reported as 225-227°. Sublimes at 120° and 20 mm Hg. Very sol in water.

Derivative

dl-Form hydrochloride.

Nomenclature

CAS number: 25333-43-1

Properties

Prisms from methanol + acetone, mp >300°.

Derivative

dl-Form acetate (ester).

Nomenclature

Aceclidine; 3-acetoxyquinuclidine; 3-quinuclidinyl acetate.
C9H15NO2; mol wt 169.22.
C 63.88%, H 8.93%, N 8.28%, O 18.91%.

Properties

Oily liq, bp0.4 73-74°, bp11 113-115°. nD25 1.4675.

Derivative

dl-Form acetate hydrochloride.

Nomenclature

CAS number: 6109-70-2
Glaucostat (Merck & Co.); Glaucotat (Chibret); Glaudin (Sifi).
C9H15NO2.HCl; mol wt 205.68.
C 52.56%, H 7.84%, N 6.81%, O 15.56%, Cl 17.24%.

Properties

Crystals, mp 166°.

Derivative

dl-Form benzilate (ester).

Nomenclature

3-Quinuclidinyl benzilate; BZ; QNB; Ro-2-3308.
C21H23NO3; mol wt 337.41.
C 74.75%, H 6.87%, N 4.15%, O 14.23%.

Description and references

Prepn: Sternbach, Kaiser, loc. cit., 2219.

Properties

Crystals from acetone-ether, mp 164-165°.

Derivative

dl-Form benzoate (ester).

Nomenclature

CAS number: 66-93-3
3-Benzoyloxyquinuclidine; 3-quinuclidinyl benzoate.
C14H17NO2; mol wt 231.29.
C 72.70%, H 7.41%, N 6.06%, O 13.83%.

Properties

Oily liquid, bp0.3 148-150°.

Derivative

dl-Form benzoate hydrochloride.

Nomenclature

CAS number: 25333-48-6
Oksilidin; oxylidine.
C14H17NO2.HCl; mol wt 267.75.
C 62.80%, H 6.78%, N 5.23%, O 11.95%, Cl 13.24%.

Properties

Crystals, mp 238-240°.

Derivative

l-Form.

Nomenclature

CAS number: 25333-42-0

Properties

Prisms from acetone, mp 220-222°. [α]D25 -2.0° (c = 6.5), -43.8° (c = 3 in 1N HCl).

Use

Benzilate (ester) has been used as an incapacitating agent in chemical warfare: Health Aspects of Chemical and Biological Weapons (WHO, Geneva, 1970) pp 49-51.

Therapeutic Category

Hypotensive; acetate (ester) as cholinergic.

Keywords

Aceclidine: Cholinergic