3-Quinuclidinol
Title: 3-Quinuclidinol
CAS Registry Number: 1619-34-7
CAS Name: 1-Azabicyclo[2.2.2]octan-3-ol
Additional Names: 3-hydroxyquinuclidine
Molecular Formula: C7H13NO
Molecular Weight: 127.18
Percent Composition: C 66.11%, H 10.30%, N 11.01%, O 12.58%
Literature 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.
 
Derivative Type: dl-Form
CAS Registry 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.
Melting point: mp 221-223° also reported as 225-227°
 
Derivative Type: dl-Form hydrochloride
CAS Registry Number: 25333-43-1
Properties: Prisms from methanol + acetone, mp >300°.
Melting point: mp >300°
 
Derivative Type: dl-Form acetate (ester)
Additional Names: Aceclidine; 3-acetoxyquinuclidine; 3-quinuclidinyl acetate
Molecular Formula: C9H15NO2
Molecular Weight: 169.22
Percent Composition: 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.
Boiling point: bp0.4 73-74°; bp11 113-115°
Index of refraction: nD25 1.4675
 
Derivative Type: dl-Form acetate hydrochloride
CAS Registry Number: 6109-70-2
Trademarks: Glaucostat (Merck & Co.); Glaucotat (Chibret); Glaudin (Sifi)
Molecular Formula: C9H15NO2.HCl
Molecular Weight: 205.68
Percent Composition: C 52.56%, H 7.84%, N 6.81%, O 15.56%, Cl 17.24%
Properties: Crystals, mp 166°.
Melting point: mp 166°
 
Derivative Type: dl-Form benzilate (ester)
Additional Names: 3-Quinuclidinyl benzilate; BZ; QNB
Manufacturers' Codes: Ro-2-3308
Molecular Formula: C21H23NO3
Molecular Weight: 337.41
Percent Composition: C 74.75%, H 6.87%, N 4.15%, O 14.23%
Literature References: Prepn: Sternbach, Kaiser, loc. cit., 2219.
Properties: Crystals from acetone-ether, mp 164-165°.
Melting point: mp 164-165°
 
Derivative Type: dl-Form benzoate (ester)
CAS Registry Number: 66-93-3
Additional Names: 3-Benzoyloxyquinuclidine; 3-quinuclidinyl benzoate
Molecular Formula: C14H17NO2
Molecular Weight: 231.29
Percent Composition: C 72.70%, H 7.41%, N 6.06%, O 13.83%
Properties: Oily liquid, bp0.3 148-150°.
Boiling point: bp0.3 148-150°
 
Derivative Type: dl-Form benzoate hydrochloride
CAS Registry Number: 25333-48-6
Additional Names: Oksilidin; oxylidine
Molecular Formula: C14H17NO2.HCl
Molecular Weight: 267.75
Percent Composition: C 62.80%, H 6.78%, N 5.23%, O 11.95%, Cl 13.24%
Properties: Crystals, mp 238-240°.
Melting point: mp 238-240°
 
Derivative Type: l-Form
CAS Registry Number: 25333-42-0
Properties: Prisms from acetone, mp 220-222°. [a]D25 -2.0° (c = 6.5), -43.8° (c = 3 in 1N HCl).
Melting point: mp 220-222°
Optical Rotation: [a]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.
Therap-Cat: Hypotensive; acetate (ester) as cholinergic.

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