N,N-Dimethylphenethylamine

Last updated
N,N-Dimethylphenethylamine
N,N-Dimethylphenethylamine.svg
Names
Preferred IUPAC name
N,N-Dimethyl-2-phenylethan-1-amine
Other names
N,N-Dimethyl-2-phenylethanamine
N,N-Dimethyl-β-phenylethylamine
N,N-DMPEA
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.156.869 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 628-613-4
PubChem CID
UNII
  • InChI=1S/C10H15N/c1-11(2)9-8-10-6-4-3-5-7-10/h3-7H,8-9H2,1-2H3
    Key: TXOFSCODFRHERQ-UHFFFAOYSA-N
  • CN(C)CCC1=CC=CC=C1
Properties
C10H15N
Molar mass 149.237 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

N,N-Dimethylphenethylamine (N,N-DMPEA) is a substituted phenethylamine that is used as a flavoring agent. It is an alkaloid that was first isolated from the orchid Eria jarensis . [1] Its aroma is described as "sweet, fishy". It is mainly used in cereal, cheese, dairy products, fish, fruit and meat. [2] It is also being used in pre-workout and bodybuilding supplements with claims of a stimulant effect. [3]

Contents

There is also evidence suggesting that N,N-DMPEA acts as a TAAR1 agonist in humans, [4] and as a 5-HT1A ligand in rats. Some less conclusive research also indicated that it had interaction with MAO-B, most likely as an enzyme substrate and not an inhibitor. [5]

N,N-DMPEA is a positional isomer of methamphetamine. Instead of the methyl group attached to the alpha position of phenylethylamine, it's attached to the nitrogen group. Both substances have the chemical formula C10H15N.

Safety

N,N-DMPEA has been found to be safe for use as a flavoring agent by the Flavor and Extract Manufacturers Association (FEMA) Expert Panel [6] and also by the Joint Expert Committee on Food Additives (JECFA) [7] —a collaboration between the Food and Agricultural Organization of the United Nations (FAO) and the World Health Organization. [8]

Legality

In the United States, N,N-DMPEA may be considered a Schedule II substance as a positional isomer of methamphetamine (C10H15N), due to the Schedule II definition of methamphetamine defined as "any quantity of methamphetamine, including its salts, isomers, and salts of isomers" [9] [10] [11]

Related Research Articles

<span class="mw-page-title-main">E number</span> Codes for food additives

E numbers, short for Europe numbers, are codes for substances used as food additives, including those found naturally in many foods such as vitamin C, for use within the European Union (EU) and European Free Trade Association (EFTA). Commonly found on food labels, their safety assessment and approval are the responsibility of the European Food Safety Authority (EFSA). The fact that an additive has an E number implies that its use was at one time permitted in products for sale in the European Single Market; some of these additives are no longer allowed today.

<span class="mw-page-title-main">Diacetyl</span> Chemical compound

Diacetyl ( dy-yuh-SEE-tuhl) (IUPAC systematic name: butanedione or butane-2,3-dione) is an organic compound with the chemical formula (CH3CO)2. It is a yellow liquid with an intensely buttery flavor. It is a vicinal diketone (two C=O groups, side-by-side). Diacetyl occurs naturally in alcoholic beverages and is added as a flavoring to some foods to impart its buttery flavor.

<span class="mw-page-title-main">Tyramine</span> Chemical compound

Tyramine, also known under several other names, is a naturally occurring trace amine derived from the amino acid tyrosine. Tyramine acts as a catecholamine releasing agent. Notably, it is unable to cross the blood-brain barrier, resulting in only non-psychoactive peripheral sympathomimetic effects following ingestion. A hypertensive crisis can result, however, from ingestion of tyramine-rich foods in conjunction with the use of monoamine oxidase inhibitors (MAOIs).

<span class="mw-page-title-main">Fumaric acid</span> Organic compound

Fumaric acid is an organic compound with the formula HO2CCH=CHCO2H. A white solid, fumaric acid occurs widely in nature. It has a fruit-like taste and has been used as a food additive. Its E number is E297. The salts and esters are known as fumarates. Fumarate can also refer to the C
4H
2O2−
4 ion (in solution). Fumaric acid is the trans isomer of butenedioic acid, while maleic acid is the cis isomer.

<span class="mw-page-title-main">Anethole</span> Chemical compound

Anethole is an organic compound that is widely used as a flavoring substance. It is a derivative of phenylpropene, a type of aromatic compound that occurs widely in nature, in essential oils. It is in the class of phenylpropanoid organic compounds. It contributes a large component of the odor and flavor of anise and fennel, anise myrtle (Myrtaceae), liquorice (Fabaceae), magnolia blossoms, and star anise (Schisandraceae). Closely related to anethole is its isomer estragole, abundant in tarragon (Asteraceae) and basil (Lamiaceae), that has a flavor reminiscent of anise. It is a colorless, fragrant, mildly volatile liquid. Anethole is only slightly soluble in water but exhibits high solubility in ethanol. This trait causes certain anise-flavored liqueurs to become opaque when diluted with water; the ouzo effect.

<span class="mw-page-title-main">Lactisole</span> Chemical compound

Lactisole is the sodium salt and commonly supplied form of 2-(4-methoxyphenoxy)propionic acid, a natural carboxylic acid found in roasted coffee beans. Like gymnemic acid, it has the property of masking sweet flavors and is used for this purpose in the food industry.

<span class="mw-page-title-main">Senomyx</span> American biotechnology company

Senomyx was an American biotechnology company that developed food additives. The company claimed to have "reverse engineered" human taste and aroma receptors. It was founded by Lubert Stryer and Paul Nevsky in 1998. On 17 Sept 2018, private Swiss company Firmenich completed the acquisition of Senomyx.

<span class="mw-page-title-main">Green S</span> Chemical compound and dye

Green S is a green synthetic coal tar triarylmethane dye with the molecular formula C27H25N2O7S2Na.

β-Methylphenethylamine Chemical compound

β-Methylphenethylamine is an organic compound of the phenethylamine class, and a positional isomer of the drug amphetamine, with which it shares some properties. In particular, both amphetamine and β-methylphenethylamine are human TAAR1 agonists. In appearance, it is a colorless or yellowish liquid.

<span class="mw-page-title-main">Disodium ribonucleotides</span> Flavor enhancer

Disodium 5'-ribonucleotides or I+G, E number E635, is a flavor enhancer which is synergistic with glutamates in creating the taste of umami. It is a mixture of disodium inosinate (IMP) and disodium guanylate (GMP) and is often used where a food already contains natural glutamates or added monosodium glutamate (MSG). It is primarily used in flavored noodles, snack foods, chips, crackers, sauces and fast foods. It is produced by combining the sodium salts of the natural compounds guanylic acid (E626) and inosinic acid (E630).

<span class="mw-page-title-main">Potassium gluconate</span> Chemical compound

Potassium gluconate is the potassium salt of the conjugate base of gluconic acid. It is also referred to as 2,3,4,5,6-pentahydroxycaproic acid potassium salt, D-gluconic acid potassium salt, or potassium D-gluconate.

1-Aminopentane is an organic compound with the formula CH3(CH2)4NH2. It is used as a solvent, as a raw material in the manufacture of a variety of other compounds, including dyes, emulsifiers, and pharmaceutical products, and as a flavoring agent.

<span class="mw-page-title-main">Buphedrone</span> Chemical compound

Buphedrone, also known as α-methylamino-butyrophenone (MABP), is a stimulant of the phenethylamine and cathinone chemical classes that was first synthesized in 1928. It is legal in most countries as a research chemical, as long as it is not intended for human consumption.

<span class="mw-page-title-main">Joint FAO/WHO Expert Committee on Food Additives</span>

The Joint FAO/WHO Expert Committee on Food Additives (JECFA) is an international scientific expert committee that is administered jointly by the Food and Agriculture Organization of the United Nations (FAO) and the World Health Organization (WHO). It has been meeting since 1956 to provide independent scientific advice pertaining to the safety evaluation of food additives. Its current scope of work now also includes the evaluation of contaminants, naturally occurring toxicants and residues of veterinary drugs in food.

<i>Acmella oleracea</i> Species of flowering plant

Acmella oleracea is a species of flowering herb in the family Asteraceae. Common names include toothache plant, Szechuan buttons, paracress, buzz buttons, tingflowers and electric daisy. Its native distribution is unclear, but it is likely derived from a Brazilian Acmella species. A small, erect plant, it grows quickly and bears gold and red inflorescences. It is frost-sensitive but perennial in warmer climates.

<span class="mw-page-title-main">Ethane-1,1-dithiol</span> Chemical compound

Ethane-1,1-dithiol is an organosulfur compound with formula CH3CH(SH)2. It is a colourless smelly liquid that is added to or found in some foods. The compound is an example of a geminal dithiol.

Decenoic acid is any mono-carboxylic acid with an unbranched chain of ten carbons connected by eight single bonds and one double bond; that is, a chemical compound with formula HO(O=)C–(CH
2)
k–CH=CH–(CH
2)
7-k–H, where k is between 0 and 7 inclusive.

<span class="mw-page-title-main">4-Methylcyclohexanemethanol</span> Chemical compound

4-Methylcyclohexanemethanol (MCHM, systematic name 4-methylcyclohexylmethanol) is an organic compound with the formula CH3C6H10CH2OH. Classified as a saturated higher alicyclic primary alcohol. Both cis and trans isomers exist, depending on the relative positions of the methyl (CH3) and hydroxymethyl (CH2OH) groups on the cyclohexane ring. Commercial samples of MCHM consists of a mixture of these isomers as well as other components that vary with the supplier.

The Food Chemicals Codex (FCC) is a collection of internationally recognized standards for the purity and identity of food ingredients.

<span class="mw-page-title-main">Trithioacetone</span> Chemical compound

Trithioacetone (2,2,4,4,6,6-hexamethyl-1,3,5-trithiane) is an organic chemical with formula C
9H
18S
3. Its covalent structure is [–C(CH
3)
2–S–]
3, that is, a six-membered ring of alternating carbon and sulfur atoms, with two methyl groups attached to each carbon. It can be viewed as a derivative of 1,3,5-trithiane, with methyl-group substituents for all of the hydrogen atoms in that parent structure.

References

  1. ↑ K. Hedman, K. Leander and B. Luning (1969). "Studies on Orchidaceae Alkaloids. XV. Phenethylamines from Eria jarensis Ames". Acta Chem. Scand. 23: 3261. doi: 10.3891/acta.chem.scand.23-3261 .
  2. ↑ Burdock, G.A. (2016). Fenaroli's Handbook of Flavor Ingredients, Sixth Edition. CRC Press. p. 499. ISBN   9781420090864 . Retrieved 2016-09-13.
  3. ↑ "Eria Jarensis Extract / N-phenethyl dimethylamine: The Next Big Thing?". blog.priceplow.com. Retrieved 2016-10-05.
  4. ↑ Wainscott DB, Little SP, Yin T, Tu Y, Rocco VP, He JX, Nelson DL (January 2007). "Pharmacologic characterization of the cloned human trace amine-associated receptor1 (TAAR1) and evidence for species differences with the rat TAAR1". The Journal of Pharmacology and Experimental Therapeutics. 320 (1): 475–485. doi:10.1124/jpet.106.112532. PMID   17038507. S2CID   10829497.
  5. ↑ Pubchem. "N,N-Dimethylphenethylamine | C10H15N - PubChem". pubchem.ncbi.nlm.nih.gov. Retrieved 2016-10-05.
  6. ↑ "Flavor and Extract Manufacturers Association (FEMA) GRAS Flavoring Substances 22". www.femaflavor.org. Retrieved 2019-01-14.
  7. ↑ "Evaluations of the Joint FAO/WHO Expert Committee on Food Additives (JECFA)". apps.who.int. Retrieved 2019-01-14.
  8. ↑ "The Joint FAO/WHO Expert Committee on Food Additives (JECFA)". www.fao.org. Retrieved 2019-01-14. The Joint FAO/WHO Expert Committee on Food Additives (JECFA) is an international expert scientific committee that is administered jointly by the Food and Agriculture Organization of the United Nations (FAO) and the World Health Organization (WHO).
  9. ↑ http://isomerdesign.com/Cdsa/FR/36FR12734.pdf [ bare URL PDF ]
  10. ↑ "21 U.S. Code § 812 - Schedules of controlled substances".
  11. ↑ https://www.govinfo.gov/content/pkg/STATUTE-84/pdf/STATUTE-84-Pg1236.pdf [ bare URL PDF ]
This page is based on this Wikipedia article
Text is available under the CC BY-SA 4.0 license; additional terms may apply.
Images, videos and audio are available under their respective licenses.