Vasicine

Last updated
Vasicine
Vasicin.svg
Names
IUPAC name
1,2,3,9-Tetrahydropyrrolo[2,1-b]quinazolin-3-ol
Other names
Peganine
Identifiers
3D model (JSmol)
PubChem CID
UNII
  • C1CN2CC3=CC=CC=C3N=C2C1O
Properties
C11H12N2O
Molar mass 188.230 g·mol−1
Melting point 210 °C (410 °F; 483 K)
Solubility in acetone, alcohol, chloroformSoluble
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Vasicine (peganine) is a quinazoline alkaloid. It is found in Justicia adhatoda , after which it is named. It is additionally found in Peganum harmala . [1]

Vasicine has been compared to theophylline both in vitro and in vivo . [2] It has also been studied in combination with the related alkaloid vasicinone. Both the alkaloids in combination (1:1) showed pronounced bronchodilatory activity in vivo and in vitro. [3] Both alkaloids are also respiratory stimulants. [3] Vasicine has a cardiac–depressant effect, while vasicinone is a weak cardiac stimulant; the effect can be normalized by combining the alkaloids. [3] [4] Vasicine is reported to have a uterine stimulant effect. [4]

Bromhexine, a synthetic compound imitating the molecular shape of vasicine[ citation needed ], is a common ingredient of cough medicine for its mucolytic properties; it increases the production of serous mucus in the respiratory tract which makes the phlegm thinner and less viscous, which allows the cilia to more easily transport the phlegm out of the lungs.

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<i>Banisteriopsis caapi</i> Species of plant

Banisteriopsis caapi, also known as, caapi, soul vine, or yagé (yage), is a South American liana of the family Malpighiaceae. It is commonly used as an ingredient of ayahuasca, a decoction with a long history of its entheogenic use and its status as a "plant teacher" among the Indigenous peoples of the Amazon rainforest.

β-Carboline Chemical compound also known as norharmane

β-Carboline (9H-pyrido[3,4-b]indole) represents the basic chemical structure for more than one hundred alkaloids and synthetic compounds. The effects of these substances depend on their respective substituent. Natural β-carbolines primarily influence brain functions but can also exhibit antioxidant effects. Synthetically designed β-carboline derivatives have recently been shown to have neuroprotective, cognitive enhancing and anti-cancer properties.

<span class="mw-page-title-main">Harmala alkaloid</span> Group of chemical compounds

Harmala alkaloids are several alkaloids that increase effects of reward system neurotransmitter dopamine by acting as monoamine oxidase inhibitors (MAOIs). These alkaloids are found in the seeds of Peganum harmala, as well as leaves of tobacco and coffee beans. The alkaloids include harmine, harmaline, harmalol, and their derivatives, which have similar chemical structures, hence the name "harmala alkaloids". These alkaloids are of interest for their use in Amazonian shamanism, where they are derived from other plants. Harmine, once known as telepathine and banisterine, is a naturally occurring beta-carboline alkaloid that is structurally related to harmaline, and also found in the vine Banisteriopsis caapi. Tetrahydroharmine is also found in B. caapi and P. harmala. Dr. Alexander Shulgin has suggested that harmine may be a breakdown product of harmaline. Harmine and harmaline are reversible inhibitors of monoamine oxidase A (RIMAs). They can stimulate the central nervous system by inhibiting the metabolism of monoamine compounds such as serotonin and norepinephrine.

<i>Peganum harmala</i> Species of plant

Peganum harmala, commonly called wild rue, Syrian rue, African rue, esfand or espand, or harmel, is a perennial, herbaceous plant, with a woody underground rootstock, of the family Nitrariaceae, usually growing in saline soils in temperate desert and Mediterranean regions. Its common English-language name came about because of a resemblance to rue. Because eating it would sicken or kill livestock, it is considered a noxious weed in a number of countries. It has become an invasive species in some regions of the western United States. The plant is popular in Middle Eastern and north African folk medicine. The alkaloids contained in the plant, including the seeds, are monoamine oxidase inhibitors.

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

Harmaline is a fluorescent indole alkaloid from the group of harmala alkaloids and beta-carbolines. It is the partly hydrogenated form of harmine.

An oneirogen, from the Greek ὄνειρος óneiros meaning "dream" and gen "to create", is a substance or other stimulus which produces or enhances dreamlike states of consciousness. This is characterized by an immersive dream state similar to REM sleep, which can range from realistic to alien or abstract.

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

Chelerythrine is a benzophenanthridine alkaloid present in the plant Chelidonium majus. It is a potent, selective, and cell-permeable protein kinase C inhibitor in vitro. And an efficacious antagonist of G-protein-coupled CB1 receptors. This molecule also exhibits anticancer qualities and it has served as a base for many potential novel drugs against cancer. Structurally, this molecule has two distinct conformations, one being a positively charged iminium form, and the other being an uncharged form, a pseudo-base.

<span class="mw-page-title-main">Indole alkaloid</span> Class of alkaloids

Indole alkaloids are a class of alkaloids containing a structural moiety of indole; many indole alkaloids also include isoprene groups and are thus called terpene indole or secologanin tryptamine alkaloids. Containing more than 4100 known different compounds, it is one of the largest classes of alkaloids. Many of them possess significant physiological activity and some of them are used in medicine. The amino acid tryptophan is the biochemical precursor of indole alkaloids.

There has been much speculation as to the botanical identity of soma or haoma. Soma is a plant described in Hindu sacred texts including the Rigveda, while haoma is a plant described in the Avesta, a collection of Zoroastrian writings. Both names are derived from the Proto-Indo-Iranian *Sauma. Proposed candidates include various species of plants and or fungi. Traditional etymology of Indian Soma is Somalata used traditionally by the Srauta Brahmins called Somayajis whereas the Avestan Haoma is an Ephedra, which are totally unconnected species sourced from different areas. European researchers suggest other plants, such as the perennial Peganum harmala, Nelumbo nucifera, Cannabis sativa, and the sugarcane species Tripidium bengalense ; while fungal candidates include the fly-agaric mushroom Amanita muscaria, the psilocybin-containing mushroom Psilocybe cubensis, and the ergot fungus Claviceps purpurea. Other scholarly proposals include mixtures of these candidates with each other and with other substances.

<i>Justicia adhatoda</i> Species of flowering plant

Justicia adhatoda commonly known in English as Malabar nut, adulsa, adhatoda, vasa, vasaka, is native to Asia.

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

Tetrahydroharman(e), also known as 1-methyl-1,2,3,4-tetrahydro-β-carboline, is a general name for one of two isomers:

  1. (1S)-1-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole
  2. Calligonine ((1R)-1-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole)
<span class="mw-page-title-main">Amiphenazole</span> Chemical compound

Amiphenazole (Daptazile) is a respiratory stimulant traditionally used as an antidote for barbiturate or opiate overdose, usually in combination with bemegride, as well as poisoning from other sedative drugs and treatment of respiratory failure from other causes. It was considered particularly useful as it could counteract the sedation and respiratory depression produced by morphine but with less effect on analgesia. It is still rarely used in medicine in some countries, although it has largely been replaced by more effective respiratory stimulants such as doxapram and specific opioid antagonists such as naloxone.

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

Harmane (harman) is a heterocyclic amine found in a variety of foods including coffee, sauces, and cooked meat. It is also present in tobacco smoke.

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

Palmatine is a protoberberine alkaloid found in several plants including Phellodendron amurense, Coptis Chinensis and Corydalis yanhusuo, Tinospora cordifolia, Tinospora sagittata, Phellodendron amurense, Stephania yunnanensis.

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

Vasicinone is a quinazoline alkaloid. It shows bronchodilator action in vitro but bronchoconstrictor action in vivo. Vasicinone was shown to have an antianaphylactic action. It has been found within Peganum harmala.

<span class="mw-page-title-main">Quinazoline alkaloids</span>

Quinazoline alkaloids are natural products from the group of alkaloids, which are chemically derived from quinazoline. Some quinazoline alkaloids show bronchodilatory effects and stimulate respiration. An abortive effect was also found for vasicine in studies on rats and rabbits.

References

  1. Moloudizargari M, Mikaili P, Aghajanshakeri S, Asghari MH, Shayegh J (July 2013). "Pharmacological and therapeutic effects of Peganum harmala and its main alkaloids". Pharmacogn Rev. 7 (14): 199–212. doi: 10.4103/0973-7847.120524 . PMC   3841998 . PMID   24347928.
  2. Nepali, Kunal; Sharma, Sahil; Ojha, Ritu; Dhar, Kanaya Lal (2012). "Vasicine and structurally related quinazolines". Medicinal Chemistry Research . 22 (1): 1–15. doi:10.1007/s00044-012-0002-5. ISSN   1054-2523. S2CID   253636554.
  3. 1 2 3 Avula, B.; et al. (2008). "Quantitative determination of vasicine and vasicinone in Adhatoda vasica by high performance capillary electrophoresis" (PDF). Die Pharmazie. 63 (1): 20–22. doi:10.1691/ph.2008.7175. PMID   18271297.
  4. 1 2 Rajani, M; Soni, S; Anandjiwala, Sheetal; Patel, G (2008). "Validation of different methods of preparation of Adhatoda vasica leaf juice by quantification of total alkaloids and vasicine". Indian Journal of Pharmaceutical Sciences. 70 (1): 36–42. doi: 10.4103/0250-474X.40329 . ISSN   0250-474X. PMC   2852058 . PMID   20390078.