Methylhexanamine (trade name Forthane , Geranamine ) or methylhexamine , commonly known as 1,3-dimethylamylamine ( 1,3-DMAA ) or just dimethylamylamine ( DMAA ), is an indirect sympathomimetic drug discovered and developed by Eli Lilly and Company and was marketed as a nasal decongestant inhaled from 1944 until it was withdrawn voluntarily from the market in 1983.
Since 2006 methylhexanamine has been sold widely under many names as a stimulant or energy-boosting food supplement under the claim that it is similar to certain compounds found in geraniums, but its safety has been questioned as a number of side effects and at least five deaths have been linked to supplements that containing methylhexanamine. It is banned by many sports authorities and government agencies.
Video Methylhexanamine
History
In April 1944, Eli Lilly and Company introduced methylhexanamine under the brand name Forthane as inhaled nasal decongestants; Lilly voluntarily recalled methylhexanamine from the market in 1983. This compound is an aliphatic amine; the pharmaceutical industry had a strong interest in compounds in this class as a nasal decongestant in the early 20th century, which caused methylhexanamine and four other similar compounds brought to market for its use: tuaminoheptane, octin, oenethyl, and propylhexedrine; octine and oenethyl are finally approved for use in maintaining high blood pressure for patients under anesthesia.
Maps Methylhexanamine
Marketing as a food supplement
Patrick Arnold reintroduced methylhexanamine in 2006 as a dietary supplement, after a late ephedrine ban in the United States in 2005. Arnold introduced it under the trademark name Geranamine , the name held by his company, Proviant Technologies. A large number of supplements that focus on fat loss and exercise energy (thermogenic or general purpose stimulants) use this ingredient along with other substances such as caffeine, a combination similar to a combination of ephedrine and caffeine.
Supplements containing methylhexanamine sometimes list "geranium oil" or "geranium extract" as a source of methylhexanamine. However, geranium oil does not contain methylhexanamine, and methylhexanamine in this supplement is added in the form of synthetic materials. Recent studies have shown that DMAA is found in some types of geranium.
Methylhexanamine is synthesized by reacting 4-methylhexan-2-one with hydroxylamine, which converts 4-methylhexan-2-one to 4-methylhexan-2-one oxime, which is reduced with hydrogen through a catalyst; The resulting methylhexanine can be purified by distillation.
Pharmacology
Methylhexanamine is an indirect sympathomimetic drug that constricts blood vessels and thus has an effect on the heart, lungs, and reproductive organs. It also causes bronchodilation, inhibits peristalsis in the intestine, and has a diuretic effect. Much of the research has been done on pharmacological effects when the drug is inhaled; Our understanding of what methylhexanamine does when taken orally is largely based on extrapolation from the activity of similar compounds. A 2013 review concluded that: "Pharmacological effects after oral intake can be expected in the lung (bronchodilation) and nasal mucosa following a single oral dose of about 4-15 mg.Harmacological effects on the heart can be expected to follow a single oral dose of about 50-75 mg The pharmacological effects on blood pressure can be expected after a single oral dose of about 100 mg. Due to the long half-life, there is a risk that repeated doses within 24-36 hours can lead to stable stronger pharmacological effects (build-up). "
Detection in body fluids
Methylhexanamine can be quantified in blood, plasma, or urine by gas or liquid chromatographic mass spectrometry to confirm the diagnosis of poisoning in hospitalized patients or to provide evidence in the investigation of medicolegal death. The concentration of methylhexanamine blood or plasma is expected to be in the range of 10-100 g/l in people taking recreational drugs, & gt; 100? G/l in a drunk patient, & & gt; 300? G/l in an acute victim overdose.
Security
LD 50 for methylhexanamine was 39Ã, mg/kg in mice and 72.5 mg/kg in mice, when administered intravenously.
The FDA has stated that methylhexanamine "is known to narrow blood vessels and arteries, which can increase blood pressure and can lead to cardiovascular events ranging from breathlessness and tighten the chest to heart attacks." Many side effects and at least five deaths have been reported to be associated with dietary supplements containing methylhexanamine.
A 2012 review by a panel hosted by the US Department of Defense to study whether the military should ban methylhexanamine supplements from stores at its base concluded that: "The evidence does not necessarily establish that substances containing DMAA are causally related to adverse medical conditions, a consistent theme among the studies is that the use of DMAA has the potential to affect cardiovascular function, such as other sympathomimetic stimulants.Without a more rigorous research design developed to evaluate the safety of DMAA, especially in patients with concurrent use of other substances, morbid conditions and high frequency use, DMAA associations with adverse medical events are uncertain The widespread use of products containing DMAA by tens of thousands of members of the Service - often combined with other substances - increases the likelihood of observing serious side effects of events, even if the overall risk of related events DMAA is low, resultin g as a result to some members of the Service and other beneficiaries. DMAA should be studied further to evaluate its safety. Data from case-control studies indicate that the frequency and amount of DMAA use and the risk of specific AME, particularly heat injury and rhabdomyolysis, need to be examined in more detail.... The Safety Review Panel recommended... to continue the ban on the sale of products containing DMAA at the Exchange and concessions. The Panel considers that the evidence supports adequate risks, even if very low, deaths or other catastrophic diseases of the Service members have used products containing DMAA, without prejudice to the benefits of these products. "
A 2012 review of the DMAA regulatory status found that "1.3-Dimethylamylamine (DMAA) is an amine pressor commonly found in dietary supplements for athletes at 25-65 mg doses. most do not leave the regulatory status of dietary supplements such as unlicensed unlicensed drugs, so we review the literature on DMAA and similar amines to deduce an effective oral dose.Based on our findings, we conclude that oral preparations with DMAA & gt 4 mg per unit of dose should be considered as effective as bronchodilators.An exceedingly limit dietary supplements are actually subject to the Drug Act and require permits.Doses higher than 100-200 mg are expected to cause serious side effects. "
Death and injury
In 2010, a 21-year-old man in New Zealand came with cerebral hemorrhage after ingesting 556 mg of methylhexanamine, caffeine, and alcohol. Health authorities in Hawaii linked cases of liver failure and one death to OxyElite Pro.
The death of Claire Squires, a runner who passed out near the finish line from April 2012 London Marathon, has been linked with methylhexanamine. The coroner states that methylhexanamine "may be an important factor" during the examination. Although, according to a friend, who has been diagnosed with an irregular heartbeat - and advised not to take methylhexanamine, it is believed that he consumed the substance through drinking an energy drink, which was then adjusted to exclude methylhexanamine.
Rule
A number of sports and state authorities have banned or severely restricted the use of methylhexanamine as a dietary supplement, due to serious concerns about its safety. These countries include the US, Canada, New Zealand, Sweden, Australia, Finland, Britain, and Brazil.
Many professional and amateur sports bodies, such as the World Anti Doping Agency, have banned methylhexanamine as a performance-enhancing agent and hung athletes who have used it.
- March 2012, minor league baseball player, Cody Stanley, suspended 50 games for proving positive after using dietary supplements.
- On June 19, 2012, the South African Drug-Free Sports Institute (SAIDS) confirmed that the winner of 2012 Comrades Marathon, Ludwick Mamabolo, proved positive using forbidden stimulants. Mamabolo could face a two-year ban and be stripped of his title if found guilty by an independent tribunal.
- In July 2012, Welsh boxer Enzo Maccarinelli was banned for six months after testing positive for methylhexanamine.
- VFL player Matthew Clark was suspended for two years after prohibited substances were detected in his system after the match in 2011.
- In August 2012, minor league baseball player Marcus Stroman suspended 50 matches for proving positive for methylhexanamine.
- On August 8, 2013, the US Weighing Auditor Brian Wilhelm received a nine-month suspension after testing positive for a drug in a urine sample starting December 2012 at the American Open.
- Anthony West's MotoGP racer is suspended for one month by the FIM International Discipline Court (CDI) on October 29, 2012 after testing positive on the drug on May 20, 2012 at the French Grand Prix. It increased retroactively to a maturity of 18 months, starting from May 20, 2012, on November 28, 2013 after being appealed by the World Anti-Doping Agency (WADA).
- In December 2013, boxer Brandon Rios, having lost a unanimous decision to Manny Pacquiao, was suspended by the China Professional Boxing Association after testing positive for the drug.
- During the 2014 Winter Olympics in Sochi, three athletes tested positive for drugs: bobsleigh brakeman and former decathlete William Frullani, German biathlete Evi Sachenbacher-Stehle and Latvian ice hockey forward Vitalijs Pavlovs.
- During the 2015 Asian Cup, Iraqi player Alaa Abdul-Zahra was subjected to investigations regarding the illegal use of the drug.
- In January 2016, Algerian footballer Kheiredine Merzougi was banned for two years by the Confederation of African Football after testing positive for the drug. However, in March 2016, FIFA international agencies confirmed that they grant an extended four-year ban to apply worldwide until January 2020.
- In November 2016, heavyweight Bermane Stiverne was fined 75,000 dollars after being tested positive for methylhexanamine by the World Boxing Council. but the WBC still let this fight happen.
- In 2017, the International Olympic Committee disqualified the 4x100 Jamaican male relay who won gold in Beijing because of Nesta Carter's positive test for methylhexanamine. It charges Usain Bolt medal.
- The Monster Energy Supercross Broc Tickle driver was suspended by the FIM International Disciplinary Court (CDI) on 13 April 2018 after testing positive for drugs after a supercross trial held in San Diego on February 10, 2018.
- On May 22, 2018, Filipino basketball player Kiefer Ravena was suspended for 18 months by FIBA ​​to compete in international competition. He was found to be positive using methylhexanamine and 1,3-dimethlybutylamine by WADA. The urine sample was taken after the Philippines vs Japan match in Manila in 2019 FIBA ​​â € <â €
Government agencies
In 2010, the US military issued a recall of all products containing methylhexanamine from all military exchange stores around the world.
In July 2011, Health Canada decided methylhexanamine was not a dietary substance, but it was a drug that needed further approval. As a result, Health Canada banned all sales of methylhexanamine.
In June 2012, the Swedish National Food Agency issued a general warning regarding the use of methylhexanamine products, resulting in a ban on sales in some parts of the country.
In July 2012, Brazil's National Health Monitoring Agency issued a warning to the general public about the dangers of products containing methylhexanamine. It also updated the list of prohibited substances to include methylhexanamine, which translates into the disposal of products containing such ingredients from the Brazilian market.
In 2012, Australia bans methylhexanamine. In New South Wales, methylhexanamine is classified as a "very dangerous substance" on toxic lists.
In August 2012, the UK Medicines and Health Products Regulatory Agency (MHRA) have ruled that a popular DMAA containing Jack3D sports supplement is an unlicensed drug product and that it and all other methylhexanamine-containing products need to be removed from the UK market amid fears of potential risks to public safety.
In 2012, the New Zealand Ministry of Health banned the sale of methylhexanamine products, in part because of the increasing use of recreation as a party pill.
In April 2013, the US Food and Drug Administration determined that methylhexanamine is potentially dangerous and does not qualify as a legal food supplement; it warns supplement makers that it is illegal to market methylhexanamine and warn consumers of potentially serious health risks associated with products containing methylhexanamine. The FDA has issued warning letters to manufacturers and distributors who continue to market products containing methylhexanamine.
See also
- 1.3-Dimethylbutylamine
- Benzedrine
- Cyclopentamine
- Levomethamphetamine
- Pseudoephedrine
References
External links
- "Potential Stimulants Dangerous to Health, FDA Warns". US Food and Drug Administration. April 11, 2013.
- Bussel, Igor I; Pavlov Jr., Andrey A (June 7, 2013). "DMAA: Efficacious but is it Safe?". Science-based Drug Blog.
Source of the article : Wikipedia
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