Chemical Properties of Sibutramine

Property	Value	Comments
Chemical name	(+/-)-Sibutramine	16Reference: Beilstein online
Autoname	{1-[1-(4-chloro-phenyl)-cyclobutyl]-3-methyl-butyl}-dimethyl-amine	16Reference: Beilstein online
Molecular Formula	C17H26Cl N	16Reference: Beilstein online
Molecular Weight	279.85	16Reference: Beilstein online
Optical Rotatory Power of the (+) enantiomer	3.3o	Type - [alpha] Concentration - 1.5g/100ml Solvent - H2O Wavelength - 589nm 17Reference: Fang et al.
Melting Point	191-192oC	Crystallised from H2O 18Reference: Jeffery et al.

This is a PDB file of Sibutramine. The exact structure was determined using Macromodel.

This however is a MOL file of a very close analogue of Sibutramine, as found in the ²⁰Cambridge Crystal Structure Database. It is shown with another molecular fragment which is unidentified at this time. It is possible that this image is of the metabolism of Sibutramine by the body - The other fragment may very well be part of a large enzyme or protein, or a model compound used to study the effect of the enzyme or protein. This model gives a better indication of how the sibutramine molecule exists in real life.

¹⁸Spectra

IR spectral frequencies of Sibutramine

vmax(KBr)/cm-1	Assignment
2963 and 2866	CH3, CH2 and CH stretch
2700	NH stretch
1492	aromatic C=C stretch
1483 and 1474	isobutyl CH bend and CH2 scissor
1428 and 1407	NCH3 bend
1395 and 1370	isobutyl CH3 bend
1092	p-substituted aromatic
1011	Aromatic in-plane bend
834 and 823	aromatic C-H out-of-plane bend

NMR chemical shifts of Sibutramine

Chemical Shift (ppm)	Assignment	Additional information
0.99	CHMe2	6H, overlapping double doublet
1.36	CH2CHMe2	Overlapping double doublet
1.65	CB CH	1H, m
1.80	CB CH	1H, m
1.90	CHMe2	1H, m
2.07	NMe	3H, d, J=4.9Hz
2.25-2.35	CB CHs	2H, m
2.6-2.75	CB CHs	2H, m
2.79	NMe	3H, d, J=5.0Hz
3.79	CHBuiNMe2	1H, t
7.46	ArH	2H, m
7.69	ArH	2H, m
9.8-9.95	NHMe2+	1H, br

Spectrum generated using gNMR and data from ¹⁸Jeffery et al.