Tuaminoheptane

Title: Tuaminoheptane
CAS Registry Number: 123-82-0
CAS Name: 2-Heptanamine
Additional Names: 1-methylhexylamine; 2-aminoheptane
Trademarks: Tuamine (Lilly)
Molecular Formula: C7H17N
Molecular Weight: 115.22
Percent Composition: C 72.97%, H 14.87%, N 12.16%
Line Formula: CH3(CH2)4CH(CH3)NH2
Literature References: a-Adrenergic agonist; topical vasoconstrictor. Prepd by heating 2-bromoheptane on steam bath with alcoholic ammonia in pressure tube: Clarke, J. Am. Chem. Soc. 21, 1027 (1899); by hydrogenation of methyl amyl ketone and ammonia in the presence of Raney nickel: Norton et al., J. Org. Chem. 19, 1054 (1954).
Properties: Volatile liq; d425 0.7600-0.7660; bp760 142-144°; nD25 1.4150-1.4200. Slightly soluble in water. pH of 1% aq soln 11.45. Freely sol in alcohol, ether, petr ether, chloroform, benzene.
Boiling point: bp760 142-144°
Index of refraction: nD25 1.4150-1.4200
Density: d425 0.7600-0.7660
Derivative Type: Hydrochloride
Molecular Formula: C7H17N.HCl
Molecular Weight: 151.68
Percent Composition: C 55.43%, H 11.96%, N 9.23%, Cl 23.37%
Properties: Needles, mp 133°. Soluble in water. pH about 5.4.
Melting point: mp 133°
Derivative Type: Sulfate
CAS Registry Number: 6411-75-2
Trademarks: Heptedrine (Bellon)
Molecular Formula: 2C7H17N.H2SO4
Molecular Weight: 328.51
Percent Composition: C 51.19%, H 11.05%, N 8.53%, S 9.76%, O 19.48%
Properties: Crystals, readily sol in water. The pH of a 1% soln is about 5.4.
Therap-Cat: Nasal decongestant.
Keywords: a-Adrenergic Agonist; Decongestant.
Tuberactinomycin Tubercidin Tuberculin Tuberin Tubulin

Tuaminoheptane
Skeletal formula of tuaminoheptane
Identifiers
CAS number 123-82-0 YesY, 6240-90-0 R YesY, 44745-29-1 S YesY
PubChem 5603, 6992808 R, 2734517 S
ChemSpider 5401 YesY, 5360930 R YesY, 2016267 S YesY
UNII Z0420GYD84 YesY
EC number 204-655-522
UN number 1993
KEGG D07371 YesY
MeSH tuamine
ChEMBL CHEMBL123693 YesY
RTECS number MQ5425000
ATC code R01AA11,
R01AB08 (combinations)
Beilstein Reference 635676, 4652352 R, 1719086 S
Jmol-3D images Image 1
Properties
Molecular formula C7H17N
Molar mass 115.22 g mol−1
Appearance Colourless liquid
Density 0.766 g/mL
Boiling point 142.1 °C; 287.7 °F; 415.2 K
log P 2.429
Refractive index (nD) 1.418–1.419
Hazards
GHS pictograms The flame pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS) The exclamation-mark pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)
GHS signal word WARNING
GHS hazard statements H226, H315, H319, H335
GHS precautionary statements P261, P305+351+338
EU classification Irritant Xi
R-phrases R10, R36/37/38
S-phrases S26, S36
Flash point 54 °C; 129 °F; 327 K
LD50 130 mg kg−1 (subcutaneous, rat)
Related compounds
Related alkanamines
  • Methylhexanamine
  • Hexamethylenediamine
Related compounds Octamoxin
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Tuaminoheptane (or tuamine) is a nasal decongestant drug which is a sympathomimetic stimulant and vasoconstrictor.[2] However, it can cause skin irritation,[3] which limits its usefulness as a nasal decongestant. Oral preparations were once available, but are no longer produced. Side effects associated with the use of tuaminoheptane can include shortness of breath, tachycardia and hypertension.

Tuaminoheptane is on the 2011 list of prohibited substances published by the World Anti-Doping Agency.