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histamine
Histamine is a naturally occurring 2-(1H-imidazol-5-yl)ethanamine involved in various biological processes and found in foods such as bananas and spinach.
General Material Description
Histamine is a biogenic amine chemically known as 2-(1H-imidazol-5-yl)ethanamine, with the molecular formula C5H9N3. It appears as a colorless to pale yellow crystalline solid, possessing an imidazole ring linked to an aminoethyl side chain. Histamine exhibits a characteristic pungent odor and is known for its presence in various natural sources including fruits and vegetables. It is widely studied and referenced in chemical and biological databases, such as ChEBI. This compound is biosynthesized in living organisms through decarboxylation of the amino acid histidine and is found commonly in plants like banana, spinach, and cantaloupe. It is also an important component in natural substances and extractives relevant to food and biological sciences.
Occurrence, Applicability & Potential Uses
Histamine occurs naturally in various plant tissues including banana fruit, cabbage leaves, cantaloupe juice, pea shoots, and spinach plants, as well as sunflower tissue cultures. Its biological occurrence extends to many organisms, where it plays diverse physiological roles. In applied contexts, histamine is primarily studied within the scope of natural substances and extractives. Although it is not used in fragrance or flavoring formulations, it is important in regulatory evaluations such as under the REACH (EU) framework, which monitors substances for safety in industrial and consumer products. The compound’s study aids understanding of food chemistry, natural extract characteristics, and potential toxicity in biological systems.
Physico-Chemical Properties Summary
Histamine exhibits a molecular weight of approximately 111.15 g/mol and features an amino group attached to an imidazole ring, imparting polarity and water solubility. Its estimated water solubility at 25 °C is high, around 1,000,000 mg/L, reflecting its hydrophilic nature. The compound has a logP value of approximately -0.7, indicating low partition into lipophilic phases. The flash point is measured near 357 °F (181 °C), suggesting stability under common laboratory conditions. These physicochemical properties influence histamine’s formulation behavior, making it primarily compatible with aqueous media and limiting volatility under ambient conditions.
FAQ
What is histamine and where is it commonly found?
Histamine is an organic compound classified as a biogenic amine with the chemical name 2-(1H-imidazol-5-yl)ethanamine. It naturally occurs in various plants such as bananas, spinach, cabbage leaves, and cantaloupe. Histamine is biosynthesized from the amino acid histidine in living organisms, contributing to several biological functions. It is also present in tissues of sunflower culture and pea shoots, highlighting its widespread distribution in nature.
How is histamine used and in which industries might it be relevant?
Histamine is mainly relevant in the context of natural substances and extractives, particularly in food chemistry and biological research. Despite its presence in edible plants, it is not approved or recommended for use in fragrance or flavor formulations. Its importance lies in monitoring and regulating natural content within food products and extracts. Regulatory frameworks such as REACH (EU) evaluate its safety profile due to concerns raised from exposure and natural accumulation.
What safety regulations apply to histamine and how is it managed?
Histamine is subject to safety evaluations by agencies including the European Food Safety Authority (EFSA) and falls under the REACH (EU) regulation. It is not permitted for use as a fragrance or flavoring agent due to toxicological concerns. Safety datasheets indicate no classified hazards under OSHA guidelines, but toxicological studies report various LD50 values depending on administration routes in animal models. Careful monitoring ensures histamine levels in foods and extracts comply with safety standards to prevent adverse effects.
US / EU / FDA / JECFA / FEMA / Scholar / Patents
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Literature & References
| 2-(1H-imidazol-5-yl)ethanamine | |
| NIST Chemistry WebBook: | Search Inchi |
| Canada Domestic Sub. List: | 51-45-6 |
| Pubchem (cid): | 774 |
| Pubchem (sid): | 134972435 |
| Pherobase: | View |
Other Information
| (IUPAC): | Atomic Weights of the Elements 2011 (pdf) |
| Videos: | The Periodic Table of Videos |
| tgsc: | Atomic Weights use for this web site |
| (IUPAC): | Periodic Table of the Elements |
| CHEBI: | View |
| CHEMBL: | View |
| Golm Metabolome Database: | Search |
| Metabolomics Database: | Search |
| KEGG (GenomeNet): | C00388 |
| HMDB (The Human Metabolome Database): | HMDB00870 |
| FooDB: | FDB012596 |
| YMDB (Yeast Metabolome Database): | YMDB01556 |
| Export Tariff Code: | 2933.29.5000 |
| MedlinePlusSupp: | View |
| VCF-Online: | VCF Volatile Compounds in Food |
| ChemSpider: | View |
| Wikipedia: | View |
| Formulations/Preparations: histamine phosphate, usp, & histamine dihydrochloridehistamine phosphate injection, usp, contains 1 mg of salt (0.36 mg of histamine base) in 1 ml. other avail prepn contain 0.275 & 2.75 mg of histamine phosphate in 1 ml (0.1 & 1 mg of histamine base in 1 ml), & are packaged in 1- or 5-ml ampules. | |
General Material Information
| Preferred name | histamine |
| Trivial Name | Histamine |
| Short Description | 2-(1H-imidazol-5-yl)ethanamine |
| Formula | C5 H9 N3 |
| CAS Number | 51-45-6 |
| Deleted CAS Number | 64422-25-9 |
| ECHA Number | 200-100-6 |
| FDA UNII | 820484N8I3 |
| Nikkaji Number | J4.117C |
| Beilstein Number | 0002012 |
| MDL | MFCD00005210 |
| Bio Activity Summary | External link |
| NMR Predictor | External link |
| Synonyms |
|
Suppliers
| Alfa Biotechnology | BOC Sciences |
| Glentham Life Sciences | Santa Cruz Biotechnology |
| Sigma-Aldrich: Sigma |
PhysChem Properties
| Material listed in food chemical codex | No |
| Molecular weight | 111.14772796631 |
| Flash Point TCC Value | 180.3 °C TCC |
| logP (o/w) | -0.7 |
| Solubility | |
| water, 1e+006 mg/L @ 25 °C (est) | Yes |
Occurrences
| (data available) |
Safety Information
Safety information
| Preferred SDS: View | |
| Hazards identification | |
| Classification of the substance or mixture | |
| GHS Classification in accordance with 29 CFR 1910 (OSHA HCS) | |
| None found. | |
| GHS Label elements, including precautionary statements | |
| Pictogram | |
| Hazard statement(s) | |
| None found. | |
| Precautionary statement(s) | |
| None found. | |
| Oral/Parenteral Toxicity: | |
| intravenous-dog LD50 7 mg/kg CARDIAC: OTHER CHANGES Indian Veterinary Journal. Vol. 57, Pg. 31, 1980. intraperitoneal-guinea pig LD50 5 mg/kg "Structure et Activite Pharmacodyanmique des Medicaments du Systeme Nerveux Vegetatif," Bovet, D., and F. Bovet-Nitti, New York, S. Karger, 1948Vol. -, Pg. 736, 1948. intravenous-guinea pig LD50 180 ug/kg Journal of Pharmacology and Experimental Therapeutics. Vol. 95, Pg. 45, 1949. oral-guinea pig LDLo 200 mg/kg LUNGS, THORAX, OR RESPIRATION: DYSPNEA "Structure et Activite Pharmacodyanmique des Medicaments du Systeme Nerveux Vegetatif," Bovet, D., and F. Bovet-Nitti, New York, S. Karger, 1948Vol. -, Pg. 718, 1948. intraperitoneal-mouse LD50 725 mg/kg British Journal of Pharmacology and Chemotherapy. Vol. 17, Pg. 137, 1961. intravenous-mouse LD50 385 mg/kg BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD BEHAVIORAL: ATAXIA LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES Kiso to Rinsho. Clinical Report. Vol. 13, Pg. 89, 1979. oral-mouse LD50 220 mg/kg Japanese Journal of Toxicology. Vol. 4, Pg. 105, 1991. intravenous-rabbit LDLo 2 mg/kg "Structure et Activite Pharmacodyanmique des Medicaments du Systeme Nerveux Vegetatif," Bovet, D., and F. Bovet-Nitti, New York, S. Karger, 1948Vol. -, Pg. 784, 1948. intravenous-rat LD50 630 mg/kg LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES LUNGS, THORAX, OR RESPIRATION: DYSPNEA Kiso to Rinsho. Clinical Report. Vol. 13, Pg. 89, 1979. | |
| Dermal Toxicity: | |
| subcutaneous-cat LDLo 34 mg/kg Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 185, Pg. 461, 1937. subcutaneous-dog LDLo 28500 ug/kg GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" LUNGS, THORAX, OR RESPIRATION: DYSPNEA BEHAVIORAL: COMA "Structure et Activite Pharmacodyanmique des Medicaments du Systeme Nerveux Vegetatif," Bovet, D., and F. Bovet-Nitti, New York, S. Karger, 1948Vol. -, Pg. 718, 1948. subcutaneous-frog LDLo 1700 mg/kg "Structure et Activite Pharmacodyanmique des Medicaments du Systeme Nerveux Vegetatif," Bovet, D., and F. Bovet-Nitti, New York, S. Karger, 1948Vol. -, Pg. 718, 1948. subcutaneous-guinea pig LDLo 8 mg/kg Farmaco, Edizione Scientifica. Vol. 9, Pg. 379, 1954. subcutaneous-mouse LD50 2500 mg/kg BEHAVIORAL: ATAXIA BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES Kiso to Rinsho. Clinical Report. Vol. 13, Pg. 89, 1979. subcutaneous-rabbit LDLo 12 mg/kg CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX) "Structure et Activite Pharmacodyanmique des Medicaments du Systeme Nerveux Vegetatif," Bovet, D., and F. Bovet-Nitti, New York, S. Karger, 1948Vol. -, Pg. 718, 1948. subcutaneous-rat LDLo 250 mg/kg AUTONOMIC NERVOUS SYSTEM: OTHER (DIRECT) PARASYMPATHOMIMETIC BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 185, Pg. 461, 1937. | |
| Inhalation Toxicity: | |
| Not determined | |
Safety in use information
| Category: | |||
| natural substances and extractives | |||
| Recommendation for histamine usage levels up to: | |||
| not for fragrance use. | |||
| Recommendation for histamine flavor usage levels up to: | |||
| not for flavor use. | |||
Safety references
| European Food Safety Authority (EFSA) reference(s): |
| Scientific Report of EFSA on the risk assessment of salts of authorised acids, phenols or alcohols for use in food contact materials [1] View page or View pdf |
| Assessment of the incidents of histamine intoxication in some EU countries View page or View pdf |
| EPI System: View |
| ClinicalTrials.gov:search |
| Daily Med:search |
| Chemical Carcinogenesis Research Information System:Search |
| AIDS Citations:Search |
| Cancer Citations:Search |
| Toxicology Citations:Search |
| EPA Substance Registry Services (TSCA):51-45-6 |
| EPA ACToR:Toxicology Data |
| EPA Substance Registry Services (SRS):Registry |
| Laboratory Chemical Safety Summary :774 |
| National Institute of Allergy and Infectious Diseases:Data |
| WGK Germany:3 |
| 2-(1H-imidazol-5-yl)ethanamine |
| Chemidplus:0000051456 |
| RTECS:MS1050000 for cas# 51-45-6 |