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Dimethylamine is an organic compound with the formula (CH₃)₂NH. This secondary amine is a colorless, flammable gas with an ammonia-like odor. Dimethylamine is commonly encountered commercially as a solution in water at concentrations up to around 40%. In 2005, an estimated 270,000 tons were produced industrially,^[5] but it is also found as a natural product.

Structure and properties[edit]

The molecule consists of a nitrogen atom with two methyl substituents and one proton. Dimethylamine is a weak base and the pKa of the ammonium salt CH₃-NH₂⁺-CH₃ is 10.73, a value above methylamine (10.64) and trimethylamine (9.79).

Dimethylamine reacts with acids to form salts, such as dimethylamine hydrochloride, an odorless white solid with a melting point of 171.5 °C. Dimethylamine is produced by catalytic reaction of methanol and ammonia at elevated temperatures and high pressure:^[6]

2 CH₃OH + NH₃ → (CH₃)₂NH + 2 H₂O

Natural Occurrence[edit]

Dimethylamine is found quite widely distributed in animals and plants, and is present in many foods at the level of a few mg/kg.^[7]

Uses[edit]

Dimethylamine is a precursor to several industrially significant compounds.^[5]^[8] It reacts with carbon disulfide to give dimethyl dithiocarbamate, a precursor to a family of chemicals widely used in the vulcanization of rubber. The solvents dimethylformamide and dimethylacetamide are derived from dimethylamine. It is raw material for the production of many agrichemicals and pharmaceuticals, such as dimefox and diphenhydramine, respectively. The chemical weapon tabun is derived from dimethylamine. The surfactant lauryl dimethylamine oxide is found in soaps and cleaning compounds. Unsymmetrical dimethylhydrazine, a rocket fuel, is prepared from dimethylamine.

Biochemistry[edit]

The German cockroach utilizes dimethylamine as a pheromone for communication.^[9]

It is an attractant for boll weevils.^[10]

Dimethylamine undergoes nitrosation under weak acid conditions to give dimethylnitrosamine. This animal carcinogen has been detected and quantified in human urine samples and it may also arise from nitrosation of dimethylamine by nitrogen oxides present in acid rain in highly industrialized countries.^{[citation needed]}

Toxicology[edit]

The toxicology of dimethylamine is discussed as part of a NIH monograph concerning dimethylamine borane. LD₅₀: 736 mg/kg (mouse, i.p.); 316 mg/kg (mouse, p.o.); 698 mg/kg (rat, p.o.); 3900 mg/kg (rat, dermal); 240 mg/kg (guinea pig or rabbit, p.o.). ^[11]

The unattributed LD (lethal dose) given in the Merck index for i.v. administration to rabbits, 4000 mg/kg, is unexpectedly high, and appears to be inconsistent with values given above.^[10]

References[edit]

^ "dimethylamine - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 16 September 2004. Identification. Retrieved 21 October 2011.
^ Hall, H.K. (1957). J. Am. Chem. Soc. 79: 5441. doi:10.1021/ja01577a030.
^ "Dimethylamine". NIST Chemistry WebBook. USA: National Institute of Standards and Technology. Retrieved 21 October 2011.
^ "Dimethylamine 38931 - ≥99.0%". Aldrich. Sigma-Aldrich Co. Retrieved 21 October 2011.
^ ^a ^b A. B. van Gysel, W. Musin "Methylamines" in Ullmann's Encyclopedia of Industrial Chemistry, 2005 Wiley-VCH Verlag, Weinheim. doi:10.1002/14356007.a16 535
^ Corbin D.R.; Schwarz S.; Sonnichsen G.C. (1997). "Methylamines synthesis: A review". Catalysis Today 37 (2): 71–102. doi:10.1016/S0920-5861(97)00003-5.
^ G. B. Neurath et al. (1977). "Primary and secondary amines in the human environment." Fd. Cosmet. Toxicol. 15 275-282.
^ Ashford's Dictionary of Industrial Chemicals, 3rd edition, 2011, pages 3284-3286
^ Zhang AQ, Mitchell SC, Smith RL (November 1998). "Dimethylamine formation in the rat from various related amine precursors". Food Chem. Toxicol. 36 (11): 923–7. doi:10.1016/S0278-6915(98)00074-X. PMID 9771553.
^ ^a ^b The Merck Index, 10th Ed. (1983), p.470, Rahway: Merck & Co.
^ Chemical Information Profile for Dimethylamine Borane, National Toxicology Program, NIEHS, NIH (2008), p.4: http://ntp.niehs.nih.gov/ntp/htdocs/Chem_Background/ExSumPdf/DimethylamineBorane508.pdf

External links[edit]

International Chemical Safety Card 0260 (gas)
International Chemical Safety Card 1485 (aqueous solution)
NIOSH Pocket Guide to Chemical Hazards 0219
Properties from Air Liquide
MSDS at airliquide.com

UpToDate Contents

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1. プロゲステロン受容体モジュレーター（PRM）の薬理学および作用機序 pharmacology and mechanism of action of progesterone receptor modulators prms

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Identification, characterization and quantification of new impurities by LC-ESI/MS/MS and LC-UV methods in rivastigmine tartrate active pharmaceutical ingredient.

Thomas S, Shandilya S, Bharati A, Paul SK, Agarwal A, Mathela CS.SourceJubilant Life Sciences Ltd., Analytical Research Department, R&D Centre, C-26, Sector-59, Noida, Uttar Pradesh 201 301, India.
Journal of pharmaceutical and biomedical analysis.J Pharm Biomed Anal.2012 Jan 5;57(1):39-51. Epub 2011 Aug 11.
Six impurities were detected at trace level in rivastigmine tartrate drug substance by a newly developed high performance liquid chromatography method. Three impurities were characterized rapidly and three impurities were found to be unknown. The unknown impurities were enriched and identified with
PMID 21880452

Simultaneous determination of Maillard reaction impurities in memantine tablets using HPLC with charged aerosol detector.

Rystov L, Chadwick R, Krock K, Wang T.SourceAnalytical Sciences, Allergan, 2525 Dupont Drive, Irvine, CA 92612, USA.
Journal of pharmaceutical and biomedical analysis.J Pharm Biomed Anal.2011 Dec 15;56(5):887-94. Epub 2011 Jul 19.
A gradient high performance liquid chromatographic (HPLC) method using charged aerosol detection (CAD) was developed for the simultaneous determination of impurities formed by the Maillard reaction in memantine tablets. These impurities were a memantine-lactose adduct (ML), a memantine-dimethylamino
PMID 21852059

Japanese Journal

フェノールフタレインを組み込んだ呈色型分子の開発

椿一典,谷間大輔,冨士薫
有機合成化学協会誌 69(3), 266-277, 2011-03-01
… Especially, host 30 with a dimethylamino group showed excellent selectivity for spermidine and spermine among other biogenic amines and high sensitivity. …
NAID 10027917072

Preparation and Characterization of CdSe-Decorated Multiwalled Carbon Nanotube Composites

Kim Dukeun,Rabbani Mohammad Mahbub,Ko Chang Hyun [他],Nam Dae-Geun,Yeum Jeong Hyun,Park Jong S.,Bae Jong-Seong,Oh Weontae
Jpn J Appl Phys 50(1), 01BJ12-01BJ12-5, 2011-01-25
… CdSe nanoparticles were stabilized by 2-(dimethylamino)ethanethiol hydrochloride to develop positive charges on their surfaces in aqueous solution. …
NAID 150000055256

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★リンクテーブル★

拡張検索	「p-dimethylaminoazobenzene」「4-dimethylaminoazobenzene」「1-dimethylaminonaphthalene-5-sulfonyl chloride」「ethyldimethylaminopropyl carbodiimide」「4-dimethylaminophenol」

「p-dimethylaminoazobenzene」

Dimethylamine
	Other names N-Methylmethanamine
Identifiers
CAS number	124-40-3
PubChem	674
ChemSpider	654
UNII	ARQ8157E0Q
EC number	204-697-4
UN number	1032
KEGG	C00543
MeSH	dimethylamine
ChEBI	CHEBI:17170
ChEMBL	CHEMBL120433
RTECS number	IP8750000
Beilstein Reference	605257
Gmelin Reference	849
3DMet	B00125
Jmol-3D images	Image 1
	SMILES CNC ;
	InChI InChI=1S/C2H7N/c1-3-2/h3H,1-2H3 ; Key: ROSDSFDQCJNGOL-UHFFFAOYSA-N ;
Properties
Molecular formula	(CH3)2NH
Appearance	Colorless gas
Odor	Ichtyal, ammoniacal
Melting point	−93.00 °C; −135.40 °F; 180.15 K
Boiling point	7 to 9 °C; 44 to 48 °F; 280 to 282 K
Solubility in water	3.540 kg L−1
log P	−0.362
Vapor pressure	170.3 kPa (at 20 °C)
kH	310 μmol Pa−1 kg−1
Acidity (pKa)	10.64
Basicity (pKb)	3.29
Thermochemistry
Std enthalpy of; formation ΔfHo298	−21–−17 kJ mol−1
Hazards
GHS pictograms
GHS signal word	DANGER
GHS hazard statements	H220, H302, H315, H318, H332, H335
GHS precautionary statements	P210, P261, P280, P305+351+338
EU Index	612-001-00-9
EU classification	F+ Xn
R-phrases	R12, R20, R37/38, R41
S-phrases	(S2), S16, S26, S39
NFPA 704	4 3 0
Flash point	−6 °C; 21 °F; 267 K
Autoignition temperature	401 °C; 754 °F; 674 K
Explosive limits	2.8–14.4%
Related compounds
Related amines	Trimethylamine; Diethylamine; Triethylamine; Diisopropylamine; Dimethylaminopropylamine; Triisopropylamine;
Related compounds	Unsymmetrical dimethylhydrazine;
	(verify) (what is: /?); Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
	Infobox references

　　[★]

p-ジメチルアミノアゾベンゼン、パラジメチルアミノアゾベンゼン

「4-dimethylaminoazobenzene」

　　[★] パラジメチルアミノアゾベンゼン。4-ジメチルアミノアゾベンゼン

「1-dimethylaminonaphthalene-5-sulfonyl chloride」

　　[★] 1-ジメチルアミノナフタレン-5-スルホニルクロリド

「ethyldimethylaminopropyl carbodiimide」

　　[★]

エチルジメチルアミノプロピルカルボジイミド

「4-dimethylaminophenol」

　　[★]

4-ジメチルアミノフェノール

[1] "dimethylamine - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 16 September 2004. Identification. Retrieved 21 October 2011.

[2] Hall, H.K. (1957). J. Am. Chem. Soc. 79: 5441. doi:10.1021/ja01577a030.

[3] "Dimethylamine". NIST Chemistry WebBook. USA: National Institute of Standards and Technology. Retrieved 21 October 2011.

[4] "Dimethylamine 38931 - ≥99.0%". Aldrich. Sigma-Aldrich Co. Retrieved 21 October 2011.

[Ullmann-5] A. B. van Gysel, W. Musin "Methylamines" in Ullmann's Encyclopedia of Industrial Chemistry, 2005 Wiley-VCH Verlag, Weinheim. doi:10.1002/14356007.a16 535

[6] Corbin D.R.; Schwarz S.; Sonnichsen G.C. (1997). "Methylamines synthesis: A review". Catalysis Today 37 (2): 71–102. doi:10.1016/S0920-5861(97)00003-5.

[7] G. B. Neurath et al. (1977). "Primary and secondary amines in the human environment." Fd. Cosmet. Toxicol. 15 275-282.

[8] Ashford's Dictionary of Industrial Chemicals, 3rd edition, 2011, pages 3284-3286

[9] Zhang AQ, Mitchell SC, Smith RL (November 1998). "Dimethylamine formation in the rat from various related amine precursors". Food Chem. Toxicol. 36 (11): 923–7. doi:10.1016/S0278-6915(98)00074-X. PMID 9771553.

[Merck-10] The Merck Index, 10th Ed. (1983), p.470, Rahway: Merck & Co.

[11] Chemical Information Profile for Dimethylamine Borane, National Toxicology Program, NIEHS, NIH (2008), p.4: http://ntp.niehs.nih.gov/ntp/htdocs/Chem_Background/ExSumPdf/DimethylamineBorane508.pdf

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dimethylamino