Tyrosine

Summary sheet: Tyrosine

Tyrosine
Chemical Nomenclature
Common names	Tyrosine, L-Tyrosine or 4-hydroxyphenylalanine
Systematic name	L-Tyrosine
Class Membership
Psychoactive class	Stimulant (Weak)
Chemical class	Phenethylamine / Amino acid
Routes of Administration
WARNING: Always start with lower doses due to differences between individual body weight, tolerance, metabolism, and personal sensitivity. See responsible use section. ⇣ Oral Dosage Threshold 300 mg Light 500 - 1000 mg Common 1000 - 2000 mg Strong 2000 - 3000 mg Heavy 3000 mg + Duration Total 2 - 4 hours Onset 30 - 90 minutes Peak 1 - 3 hours After effects 6 - 12 hours DISCLAIMER: PW's dosage information is gathered from users and resources for educational purposes only. It is not a recommendation and should be verified with other sources for accuracy.
Interactions
Alcohol
DXM
MXE
MDMA
Stimulants
25x-NBOMe
25x-NBOH
Tramadol
MAOIs

Tyrosine (also known as L-Tyrosine and 4-hydroxyphenylalanine) is a non-essential amino acid that serves a precursor to dopamine, adrenaline and norepinephrine in the human body. As a supplement, it is reported to act as a mild stimulant. It is also one of the 22 amino acids that are used by cells to synthesize proteins and is abundant in many high-protein foods, such as chicken, turkey, fish, cottage cheese, cheese, yogurt, almonds, milk, avocados, bananas, peanuts, pumpkin seeds, sesame seeds and soy products.

Some evidence suggests tyrosine supplementation can affect performance on working memory tasks under certain conditions, especially stress. Tyrosine may enhance convergent (double-task) thinking. In one study, tyrosine even seemed to reverse some of the detrimental effects of sleep deprivation on cognitive performance. However, if tyrosine increases working memory performance by elevating catecholamine levels, the effect could easily be short-lived. Some animal studies have shown dopamine levels quickly return to baseline.

Chemistry

Tyrosine is a non-essential phenylalanine-derived amino acid. Tyrosine's structure comprises a para-hydroxylated phenyl ring connected to a pentanoic acid group, which is a five member carbon chain with a carboxyl (C(=O)OH) group on the terminal carbon. This pentanoic acid chain is substituted at R₂ with an amino group in levorotary orientation.

Three structural isomers of L-tyrosine are known. In addition to the common amino acid L-tyrosine, which is the para isomer (para-tyr, p-tyr or 4-hydroxyphenylalanine), there are two additional regioisomers, namely meta-tyrosine (also known as 3-hydroxyphenylalanine, L-m-tyrosine, and m-tyr) and ortho-tyrosine (o-tyr or 2-hydroxyphenylalanine), that occur in nature. The m-tyr and o-tyr isomers, which are rare, arise through non-enzymatic free-radical hydroxylation of phenylalanine under conditions of oxidative stress.

In plants and most microorganisms, tyr is produced via prephenate, an intermediate on the shikimate pathway. Prephenate is oxidatively decarboxylated with retention of the hydroxyl group to give p-hydroxyphenylpyruvate, which is transaminated using glutamate as the nitrogen source to give tyrosine and α-ketoglutarate.

Mammals synthesize tyrosine from the essential amino acid phenylalanine (phe), which is derived from food. The conversion of phe to tyr is catalyzed by the enzyme phenylalanine hydroxylase, a monooxygenase. This enzyme catalyzes the reaction causing the addition of a hydroxyl group to the end of the 6-carbon aromatic ring of phenylalanine, such that it becomes tyrosine.

Pharmacology

This diagram represents the mechanism for tyrosine conversion into numerous catecholamines.

The effects of tyrosine as a supplement or psychoactive compound are due to it being a precursor to catecholamine neurotransmitters. Supplemental L-Tyrosine is converted by the body into L-DOPA which is then decarboxylated into dopamine, which later turns into norepinephrine and is then finally converted to epinephrine. This means it effectively boosts the levels of these neurotransmitters in the brain, resulting in stimulating and euphoric effects. These three neurotransmitters are collectively referred to as "catecholamines."

The process of catecholamine synthesis within the body is limited to a localized substrate pool, meaning that the subjective effects of tyrosine can often reach an "upper-limit" at heavy dosages in which additional supplementation for the purposes of intensify one's stimulation becomes ineffective.

Aside from being a proteinogenic amino acid, tyrosine has a special role by virtue of the phenol functionality. It occurs in proteins that are part of signal transduction processes and functions as a receiver of phosphate groups that are transferred by way of protein kinases. Phosphorylation of the hydroxyl group can change the activity of the target protein, or may form part of a signaling cascade via SH2 domain binding.

Subjective effects

In comparison to traditional stimulants such as amphetamine and methylphenidate, tyrosine can be described as more "natural" feeling, less jittery, and with fewer side effects and a milder come down or "crash." It is significantly less forced, with no distinct body high. It is also less euphoric and recreational but more functional.

Disclaimer: The effects listed below cite the Subjective Effect Index (SEI), a research literature based on anecdotal reports and the personal experiences of PsychonautWiki contributors. As a result, they should be regarded with a healthy degree of skepticism. It is worth noting that these effects will not necessarily occur in a predictable or reliable manner, although higher doses are more liable to induce the full spectrum of effects. Likewise, adverse effects become much more likely with higher doses and may include addiction, serious injury, or death.

Physical effects

• • Stimulation
  • Appetite suppression
  • Headache - This effect is usually only present at heavy doses
  • Nausea - This effect is usually only present at heavy doses

After effects

• The effects which occur during the offset of a stimulant experience generally feel negative and uncomfortable in comparison to the effects which occurred during its peak. This is often referred to as a "comedown" and occurs because of neurotransmitter depletion. It is significantly less intensive and uncomfortable with tyrosine in comparison to other more traditional stimulants such as amphetamine or methylphenidate, but it still exists and its effects commonly include:
  • Cognitive fatigue
  • Thought deceleration
  • Anxiety
  • Depression
  • Wakefulness
  • Irritability

Cognitive effects

• • Anxiety suppression
  • Analysis enhancement
  • Cognitive euphoria - Tyrosine can cause mild euphoria at strong doses
  • Creativity enhancement
  • Focus enhancement
  • Increased libido
  • Increased music appreciation
  • Wakefulness
  • Memory enhancement
  • Thought acceleration
  • Motivation enhancement
  • Stamina enhancement

Experience reports

There are currently no anecdotal reports which describe the effects of this compound within our experience index. Additional experience reports can be found here:

• Erowid Experience Vaults: Tyrosine

Toxicity and harm potential

Tyrosine is physically safe, is not known to cause brain damage, and has an extremely low toxicity relative to dose. Similar to many other nootropic drugs, there are relatively few physical side effects associated with acute tyrosine exposure. Various studies have shown that in reasonable doses in a careful context, it presents no negative cognitive, psychiatric or toxic physical consequences of any sort. However, it is still strongly recommended that one use harm reduction practices when using this drug.

Tolerance and addiction potential

Tyrosine may potentially be mildly habit forming and the desire to use it may actually increase with use. This is because of its dopaminergic properties. However, in comparison to other more traditional stimulants such as amphetamine or methylphenidate, it is not nearly as addictive or compulsive.

Tolerance to the effects of tyrosine are quickly built after repeated and frequent usage. After that, it takes about 7 days for the tolerance to be reduced to half and 14 days to be back at baseline (in the absence of further consumption). Tyrosine presents cross-tolerance with other dopaminergic stimulants, meaning that after the consumption of tyrosine, most other stimulant compounds will have a reduced effect.

Dangerous interactions

Although many psychoactive substances are reasonably safe to use on their own, they can suddenly become dangerous or even life-threatening when combined with other substances. The following list includes some known dangerous combinations (although it is not guaranteed to include all of them). Independent research (e.g. Google, DuckDuckGo) should always be conducted to ensure that a combination of two or more substances is safe to consume. Some of the listed interactions have been sourced from TripSit.

• Stimulants - Tyrosine is stimulatory on its own. Therefore, it may theoretically interact with other stimulatory pharmaceuticals or supplements and cause dangerously high blood pressure or heartrate.
• 25x-NBOMe & 25x-NBOH - Members of the 25x family are highly stimulating and physically straining. Combinations with stimulants should be avoided due to the risk of excessive stimulation. This can result in panic attacks, thought loops, seizures, increased blood pressure, vasoconstriction, and heart failure in extreme cases.
• Alcohol - Alcohol can be dangerous to combine with stimulants due to the risk of accidental over-intoxication. Stimulants mask the sedative effects of alcohol, which is the main factor people use to assess their degree of intoxication. Once the stimulant wears off, the depressant effects of alcohol are left unopposed, which can result in blackouts and respiratory depression. If combined, one should strictly limit themselves to only drinking a certain amount of alcohol per hour.
• DXM - Combinations with DXM should be handled with extreme care due to DXM's effects on serotonin and norepinephrine reuptake. This can lead to panic attacks, hypertensive crisis, or serotonin syndrome with stimulants that increase levels of serotonin (MDMA, methylone, mephedrone, etc.). Monitor blood pressure carefully and avoid strenuous physical activity.
• MDMA - The neurotoxic effects of MDMA may be increased when combined with other stimulants. There is also a risk of excessive heart strain.
• MXE - Combinations with MXE may dangerously elevate blood pressure and increase the risk of psychosis.
• Stimulants - Tyrosine can be potentially dangerous in combination with other stimulants like cocaine as they can increase one's heart rate and blood pressure to dangerous levels.
• Tramadol - Tramadol lowers the seizure threshold. Combinations with stimulants may further increase this risk.
• MDMA - The neurotoxic effects of MDMA may be increased when combined with amphetamine and other stimulants.

• MAOIs - This combination may increase the amount of neurotransmitters such as dopamine to dangerous or even fatal levels. Examples include syrian rue, banisteriopsis caapi, and some antidepressants.
• Cocaine - This combination may increase strain on the heart.

Legal status

This legality section is a stub. As such, it may contain incomplete or wrong information. You can help by expanding it.

Tyrosine is unscheduled across the world and is not known to be specifically illegal within any country.

See also

• Nootropic
• Dopamine
• Stimulant

External links

• Tyrosine (Wikipedia)
• Tyrosine (Isomer Design)
• Tyrosine (Examine)