1,3-dimethylbutylamine

Structural formula
( S ) -enantiomer (left) and ( R ) -enantiomer (right) of DMBA
General
Surname	1,3-dimethylbutylamine
other names	4-methyl-2-aminopentane ( IUPAC ) DMBA 4-AMP Pentergy
Molecular formula	C 6 H 11 N
Brief description	colorless liquid with an amine-like odor
External identifiers / databases
CAS number 108-09-8 EC number 203-549-6 ECHA InfoCard 100.003.227 PubChem 7908 ChemSpider 7620 Wikidata Q19595727
properties
Molar mass	101.19 g mol −1
Physical state	liquid
density	0.75 g cm −3 (20 ° C)
boiling point	106 ° C
Vapor pressure	145 hPa (50 ° C)
solubility	easily soluble in water
Refractive index	1.4085
safety instructions
GHS labeling of hazardous substances danger H and P phrases H: 225-302-314 P: 210-260-280-305 + 351 + 338-370 + 378-403 + 235
Toxicological data	470 mg kg −1 ( LD 50 ,  mouse ,  oral ) 80 mg kg −1 ( LD 50 ,  mouse ,  iv ) 600 mg kg −1 ( LD 50 ,  rabbit ,  transdermal )
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

1,3-Dimethylbutylamine (also: DMBA ) is an organic compound from the group of aliphatic amines . The compound is related to methylhexanamine (DMAA).

presentation

By reacting 4-methyl-2-pentanone with ammonium formate by means of a Pd / C - catalyst can be obtain the compound in high yields. The chiral representation of the compound can take place enzymatically .

properties

The compound was marketed under trade names such as 4-AMP or Pentergy in diet supplements for performance enhancement and in diet products. Furthermore, preparations were sold which had advertised an increase in mental abilities. After cases with undesirable side effects such as restlessness or the urge to move after taking DMBA-containing preparations occurred in October 2014 in the Netherlands , the BVL announced in a statement in November 2014 that preparations containing the compound were not marketable. In the opinion of the Federal Office, approval as a novel food is necessary for preparations containing DMBA, which is currently (2019) not available. As a result, preparations containing DMBA were withdrawn from the European market. Clinical studies on humans do not exist for this substance.

Manufacturers of dietary supplements often state the leaves of the tea bush as the natural origin of the substance . However, several studies have been able to demonstrate using chromatographic methods such as UHPLC , HPTLC or chiral GC-MS that the compound does not occur in these.

Individual evidence

1. ↑ ^{a b c d e f g} Entry on 1,3-dimethylbutylamine in the GESTIS substance database of the IFA , accessed on March 28, 2019 (JavaScript required)
2. ↑ ^{a b c} data sheet 1,3-dimethylbutylamine from Sigma-Aldrich , accessed on March 28, 2019 ( PDF ).
3. ↑ ^{a b c} Entry on 1,3-dimethylbutylamine. In: Römpp Online . Georg Thieme Verlag, accessed on March 28, 2019.
4. ↑ Michael J. Abrahamson, Eduardo Vázquez ‐ Figueroa, Nicholas B. Woodall, Jeffrey C. Moore, Andreas S. Bommarius: Development of an Amine Dehydrogenase for Synthesis of Chiral Amines . In: Angewandte Chemie International Edition . tape 51 , no. March 16 , 2002, doi : 10.1002 / anie.201107813 .
5. ↑ Federal Office for Consumer Protection and Food Safety (Ed.): Food supplements with 1,3-dimethylbutylamine (DMBA) are not marketable . November 10, 2014 ( bund.de [PDF; 274 kB ; accessed on March 28, 2019]).
6. ↑ Dr. André Said: DMBA no longer marketable . In: Deutsche Apothekerzeitung . No. 10 , March 2015, p. 30 ( deutsche-apotheker-zeitung.de [accessed on March 28, 2019]).
7. ^ Pieter A. Cohen, John C. Travis, Bastiaan J. Venhuis: A synthetic stimulant never tested in humans, 1,3-dimethylbutylamine (DMBA), is identified in multiple dietary supplements . In: Drug Testing and Analysis . tape 7 , no. 1 , July 2015, doi : 10.1002 / dta.1735 , PMID 25293509 ( Open Access ).
8. ↑ Bharathi Avula, Mei Wang, Satyanarayanaraju Sagi, Pieter A. Cohen, Yan-Hong Wang, Pradeep Lasonkar, Amar G. Chittiboyina, Wei Feng, Ikhlas A. Khan: Identification and quantification of 1,3-dimethylbutylamine (DMBA) from Camellia sinensis tea leaves and dietary supplements . In: Journal of Pharmaceutical and Biomedical Analysis . tape 110 , November 10, 2015, p. 159–168 , doi : 10.1016 / j.jpba.2015.07.004 .
9. ↑ Yan-Hong Wang, Mei Wang, Bharathi Avula, Satyanarayanaraju Sagi: Characterization and quantitation of 1, 3-dimethylbutylamine, caffeine, theobromine, theophylline, and eight catechins from tea varieties using LC-UV / MS . In: Planta Medica . tape 81 , no. 5 , 2015, doi : 10.1055 / s-0035-1545155 .