Harmalina

Harmalina
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Nome IUPAC 7-metoxi-1-metil-4,9-diidro-3H-pirido[3,4-b]-indol
Identificadores
Número CAS 304-21-2
PubChem 5280951
SMILES
Propriedades
Fórmula molecular C13H14N2O
Massa molar 214,263 g/mol
Ponto de fusão

232–234 °C[1]

Compostos relacionados
Compostos relacionados Harmina (o anel hexagonal com o N é aromático)
Página de dados suplementares
Estrutura e propriedades n, εr, etc.
Dados termodinâmicos Phase behaviour
Solid, liquid, gas
Dados espectrais UV, IV, RMN, EM
Exceto onde denotado, os dados referem-se a
materiais sob condições normais de temperatura e pressão
Referências e avisos gerais sobre esta caixa.
Alerta sobre risco à saúde.

A harmalina é um alcalóide indólico fluorescente e psicoativo, do grupo dos harmanos e beta-carbolinas. É a forma reduzida e hidratada da harmina

Fontes naturais

Várias plantas contêm harmalina, inclusive o cipó-mariri (Banisteriopsis caapi, um dos ingredientes do ayahuasca) e a harmala (Peganum harmala). Também é encontrada no maracujá e no tabaco.[2]

Efeitos

A harmalina é um estimulante do sistema nervoso central e um inibidor reversível da monoamina oxidase subtipo A (IRMA).[3] Sua ligação à enzima é fraca o suficiente para que esta fique com seu sítio reacional livre para processar outras substâncias, como a tiramina — os inibidores reversíveis dessa enzima se ligam tão fortemente a ela que o organismo demora semanas para repô-la. Por ser um inibidor reversível da MAO-A, ela compete com a tiramina pela ligação à enzima MAO-A; por isso, alimentos contendo tiramina podem ser consumidos com segurança (vinho e queijos amarelos deveriam ser evitados 12 h antes de consumir a substância).[4] Durante o uso da harmalina, portanto, o risco de crises hipertensivas decorrentes da ingestão de comidas que contêm tiramina é portanto potencialmente baixo em comparação com inibidores irreversíveis, especialmente depois de 24 h da ingestão desses alimentos.

Dependendo da dosagem, a harmalina induz temporariamente a alucinações onirofrênicas e a ataxia. A harmalina, no pico de sua dose segura, tem propriedades alucinógenas, mas os efeitos são substancialmente diferentes dos alucinógenos clássicos. Uma vez que a harmalina é um inibidor reversível da monoamina oxidase, é muito possível que ela aumente perigosamente o efeito de algumas drogas. Sabe-se que a harmalina não causa dependência física ou psicológica.

Fluorescência da harmina e da harmalina sob luz ultravioleta. As três extrações indicam que a do meio tem maior concentração dos dois compostos.

Há estudos para que a harmalina seja usada para tratamento de diversas dependências químicas, juntamento com outras β-carbolinas. [5]

Tem-se demonstrado que a harmalina pode induzir efeitos vasodilatadores em aortas isoladas de ratos.[6]

A harmalina tem efeito tanto protetor como tóxico para os neurônios.[5]

História

Em 1841, a harmalina foi isolada a partir da Peganum harmala por Goegel. Hasenfratz a sintetizou pela primeira vez em 1930.[5]

Referências

  1. ↑ Data from the Sigma Aldrich Catalog (German)
  2. ↑ SHULGIN, Alexander; SHULGIN Ann. TiHKAL: the continuation. Berkeley, Transform Press: 1997, pp. 713–4. ISBN 0963009699.
  3. ↑ MASSARO, Edward J (2002). Handbook of neurotoxicology. Totowa, EUA: Humana Press. 237 páginas. ISBN 0-89603-796-7 
  4. ↑ YOUDIM M B, WEINSTOCK M (2004). «Therapeutic applications of selective and non-selective inhibitors of monoamine oxidase A and B that do not cause significant tyramine potentiation». Neurotoxicology. 25 (1–2). pp. 243–50. PMID 14697899. doi:10.1016/S0161-813X(03)00103-7 
  5. ↑ a b c Method of treating chemical dependency using .beta.-carboline alkaloids, derivatives and salts thereof
  6. ↑ BERROUGUI H, MARTIN-CORDERO C, KHALIL A, HMAMOUCHI M, ETTAIB A, MARHUENDA E, HERRERA M D (2006). «Vasorelaxant effects of harmine and harmaline extracted from Peganum harmala L. seeds in isolated rat aorta». Pharmacol res. 54 (2). pp. 150–7. doi:10.1016/j.phrs.2006.04.001 

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