
IUPAC name Tyrosine
Systematic IUPAC name 2-Amino-3-(4-hydroxyphenyl)propanoic acid
CAS Number
- 60-18-4 (L)
3D model (JSmol)
- Interactive image
- Zwitterion: Interactive image
ChEBI
- CHEBI:17895
ChEMBL
- ChEMBL925
ChemSpider
- 5833
DrugBank
- DB00135
ECHA InfoCard
100.000.419
IUPHAR/BPS
- 4791
KEGG
- C00082
PubChem CID
- 6057
UNII
- 42HK56048U
CompTox Dashboard (EPA)
- DTXSID1023730
InChI
InChI=1S/C9H11NO3/c10-8(9(12)13)5-6-1-3-7(11)4-2-6/h1-4,8,11H,5,10H2,(H,12,13)/t8-/m0/s1Key:OUYCCCASQSFEME-QMMMGPOBSA-N
Key:OUYCCCASQSFEME-UHFFFAOYSA-N
Key:OUYCCCASQSFEME-MRVPVSSYSA-N
NC@@HC(O)=O
Zwitterion: [NH3+]C@@HC([O-])=O
Chemical formula
C9H11NO3
Molar mass
181.191g·mol
Appearance
white solid
Solubility in water
45.3 mg/100 mL
Magnetic susceptibility ()
−105.3·10 cm/mol
Hazards
NFPA 704 (firediamond)
1 1 0
Supplementary data page
Tyrosine (data page)
Except where otherwise noted, data are given for materials in their standard state (at 25°C [77°F], 100kPa).
Infobox references
L-Tyrosine or tyrosine (symbol Tyr or Y) or 4-hydroxyphenylalanine is one of the 20 standard amino acids that are used by cells to synthesize proteins. It is a conditionally essential amino acid with a polar side group. The word "tyrosine" is from the Greek tyrós, meaning cheese, as it was first discovered in 1846 by German chemist Justus von Liebig in the protein casein from cheese. It is called tyrosyl when referred to as a functional group or side chain. While tyrosine is generally classified as a hydrophobic amino acid, it is more hydrophilic than phenylalanine. It is encoded by the codons UAC and UAU in messenger RNA.
The one-letter symbol Y was assigned to tyrosine for being alphabetically nearest of those letters available. Note that T was assigned to the structurally simpler threonine, U was avoided for its similarity with V for valine, W was assigned to tryptophan, while X was reserved for undetermined or atypical amino acids. The mnemonic tYrosine was also proposed.
Safety at a Glance
- Toxicity: Tyrosine is physically safe, is not known to cause brain damage, and has an extremely low toxicity relative to dose. ...
- Start with a low dose and wait for onset before redosing
- Test your substance with reagent kits when possible
- Never use alone — have a sober person present
If someone is in crisis, call 911 or Poison Control: 1-800-222-1222
Dosage
Oral
Duration
Oral
Total: 3 hrs – 6 hrsHow It Feels
L-tyrosine's subjective effects are best understood as situational insurance rather than an acute experience. Under ordinary resting conditions, taking L-tyrosine produces no perceptible effect. There is no shift in mood, no change in alertness, no physical sensation. The amino acid is absorbed, enters the bloodstream, crosses into the brain, and joins the existing pool of dopamine precursors, where it waits. The experience of L-tyrosine is the experience of what does not happen when you need it to not happen.
Under conditions of stress, sleep deprivation, or sustained cognitive demand, the supplemental tyrosine makes its presence known indirectly. The decline in focus that normally accompanies exhaustion may be slightly attenuated. The irritability and emotional flatness of sleep deprivation may be marginally softened. The ability to sustain effortful cognitive work under pressure may persist a bit longer before breaking down. These effects are subtle and context-dependent, becoming apparent primarily in the gap between expected deterioration and actual performance.
There is a very mild mood-supporting quality that some users report under conditions of acute stress. The world feels fractionally less overwhelming, decisions feel fractionally more manageable, and the emotional weight of demanding situations is marginally reduced. This is not euphoria or even mood elevation in any conventional sense. It is the prevention of mood deterioration, a pharmacological floor beneath which the stress response cannot push you quite so far.
Physically, L-tyrosine is undetectable. There are no side effects, no physical sensations, and no changes in any measurable physiological parameter. The compound is a dietary amino acid, and the body treats it as such. There is no duration to speak of because there is no onset. There is no comedown because there is no high. The value of L-tyrosine lies entirely in its utility as a neurochemical buffer, quietly maintaining dopaminergic function during periods when the brain's demands exceed its supply. It is the nutritional equivalent of an emergency fund: invisible and seemingly pointless until the moment it is needed.
Subjective Effects
The effects listed below are based on the Subjective Effect Index (SEI), an open research literature based on anecdotal reports and personal analyses. They should be viewed with a healthy degree of skepticism. 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.
Physical Effects
Physical(12)
- Appetite suppression— A distinct decrease in hunger and desire to eat, ranging from reduced interest in food to complete d...
- Headache— A painful sensation of pressure, throbbing, or aching in the head that can range from a dull backgro...
- Increased blood pressure— Increased blood pressure (hypertension) is an elevation of arterial pressure above the normal 120/80...
- Increased libido— A marked enhancement of sexual desire, arousal, and sensitivity to erotic stimuli that can range fro...
- Nausea— An uncomfortable sensation of queasiness and stomach discomfort that may or may not lead to vomiting...
- Physical euphoria— An intensely pleasurable bodily sensation that can manifest as waves of warmth, tingling electricity...
- Respiratory depression— A dangerous slowing and shallowing of breathing that can progress from barely noticeable reductions ...
- Seizure— Uncontrolled brain electrical activity causing convulsions and loss of consciousness -- a life-threa...
- Serotonin syndrome— Serotonin syndrome is a potentially fatal medical emergency caused by excessive serotonergic activit...
- Stamina enhancement— Stamina enhancement is an increase in one's ability to sustain physical and mental exertion over ext...
- Stimulation— A state of heightened physical and mental energy characterized by increased wakefulness, elevated mo...
- Vasoconstriction— A narrowing of blood vessels throughout the body that produces sensations of cold extremities, tingl...
Cognitive & Perceptual Effects
Cognitive(20)
- Amnesia— A complete or partial inability to form new memories or recall existing ones during and after substa...
- Analysis enhancement— A perceived improvement in one's ability to logically deconstruct concepts, recognize patterns, and ...
- Anxiety— Intense feelings of apprehension, worry, and dread that can range from a subtle background unease to...
- Anxiety suppression— A partial to complete suppression of anxiety and general unease, producing a calm, relaxed mental st...
- Cognitive euphoria— A cognitive and emotional state of intense well-being, elation, happiness, and joy that manifests as...
- Cognitive fatigue— Mental exhaustion and difficulty sustaining thought after intense cognitive experiences, common duri...
- Creativity enhancement— An increase in the ability to imagine new ideas, overcome creative blocks, think about existing conc...
- Delusion— A delusion is a fixed, false belief that is held with unshakeable certainty and is impervious to con...
- Depression— A persistent state of low mood, emotional numbness, hopelessness, and diminished interest or pleasur...
- Focus enhancement— An enhanced ability to direct and sustain attention on a single task or stimulus with unusual clarit...
- Irritability— Irritability is a sustained state of emotional reactivity in which the threshold for annoyance, frus...
- Mania— Abnormally elevated mood, energy, and activity with impulsive behavior and grandiosity, associated w...
- Memory enhancement— Memory enhancement is a state of improved mnemonic function in which past memories become unusually ...
- Motivation enhancement— A heightened sense of drive, ambition, and willingness to accomplish tasks, making productive effort...
- Panic attack— A panic attack is a discrete episode of acute, overwhelming fear or terror that arises suddenly and ...
- Psychosis— Psychosis is a serious psychiatric state involving a fundamental break from consensus reality — char...
- Thought acceleration— The experience of thoughts occurring at a dramatically increased rate, as if the mind has been shift...
- Thought deceleration— The experience of thoughts occurring at a markedly reduced pace, as if the mind has been placed into...
- Thought loops— Becoming trapped in a repeating cycle of thoughts, actions, and emotions that loops every few second...
- Wakefulness— An increased ability to stay awake and alert without the desire to sleep. Distinct from stimulation ...
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.
Interactions
No documented interactions.
History
L-Tyrosine was first isolated from casein (milk protein) in 1846 by the German chemist Justus von Liebig. The name derives from the Greek tyros (cheese). Its role as a catecholamine precursor was established in the mid-20th century as the dopamine/norepinephrine/epinephrine biosynthetic pathway was elucidated.
The pivotal research on tyrosine for stress-related cognitive performance came from the US military. Harris Lieberman and colleagues at the US Army Research Institute of Environmental Medicine (USARIEM) demonstrated in the 1990s that tyrosine supplementation prevented cognitive decline during sustained military operations, cold exposure, and sleep deprivation. A 1989 study showed that tyrosine protected cognitive performance during a 4.5-hour cold-water immersion that severely impaired performance in the control group.
Subsequent military and academic research confirmed that tyrosine's cognitive benefits are most pronounced under challenging conditions (stress, multitasking, sleep deprivation) where catecholamine demands are high, while effects under normal resting conditions are minimal.
Harm Reduction
L-Tyrosine is generally well-tolerated at standard doses of 500-2000mg daily. Take on an empty stomach for best absorption, ideally in the morning. Avoid combining with MAOIs, as tyrosine is a precursor to catecholamines and this combination could cause dangerous blood pressure elevation. Those with hyperthyroidism should consult a doctor before supplementing, as tyrosine is also a precursor to thyroid hormones. Do not take alongside levodopa (for Parkinson's) without medical supervision, as they compete for absorption.
Toxicity & Safety
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
Warning: Many psychoactive substances that are reasonably safe to use on their own can suddenly become dangerous and even life-threatening when combined with certain other substances. The following list provides some known dangerous interactions (although it is not guaranteed to include all of them).
Always conduct independent research (e.g. Google, DuckDuckGo, PubMed) 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 - 25x compounds are highly stimulating and physically straining. Combinations with Tyrosine should be strictly avoided due to the risk of excessive stimulation and heart strain. This can result in increased blood pressure, vasoconstriction, panic attacks, thought loops, seizures, and heart failure in extreme cases.
Alcohol - Combining alcohol with stimulants can be dangerous due to the risk of accidental over-intoxication. Stimulants mask alcohol's depressant effects, which is what most people use to assess their degree of intoxication. Once the stimulant wears off, the depressant effects will be left unopposed, which can result in blackouts and severe respiratory depression. If mixing, the user should strictly limit themselves to only drinking a certain amount of alcohol per hour.
DXM - Combinations with DXM should be avoided due to its inhibiting effects on serotonin and norepinephrine reuptake. There is an increased risk of panic attacks and hypertensive crisis, or serotonin syndrome with serotonin releasers (MDMA, methylone, mephedrone, etc.). Monitor blood pressure carefully and avoid strenuous physical activity.
MDMA - Any neurotoxic effects of MDMA are likely to be increased when other stimulants are present. There is also a risk of excessive blood pressure and heart strain (cardiotoxicity).
MXE - Some reports suggest combinations with MXE may dangerously increase blood pressure and increase the risk of mania and psychosis.
Dissociatives - Both classes carry a risk of delusions, mania and psychosis, and these risk may be multiplied when combined.
Stimulants - Tyrosine may be dangerous to combine with other stimulants like cocaine as they can increase one's heart rate and blood pressure to dangerous levels.
Tramadol - Tramadol is known to lower the seizure threshold and 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.
Addiction Potential
No addiction potential. Unlike dopaminergic stimulants, tyrosine supplementation does not cause euphoria or reward pathway activation.
Tolerance
| Full | Not applicable — nutritional supplement |
| Half | N/A |
| Zero | N/A |
Cross-tolerances
Legal Status
Tyrosine is unscheduled across the world and is not known to be specifically illegal within any country.
Tips (5)
Cycle L-Tyrosine usage to prevent tolerance and dependence. Most nootropics benefit from periodic breaks (e.g., 5 days on / 2 days off, or 3 weeks on / 1 week off) to maintain effectiveness.
Standard dosing is 500-2000mg per day. Start at 500mg on an empty stomach and assess response over a few days before increasing. Take it in the morning — evening dosing can interfere with sleep in some people since it supports alertness-promoting catecholamines.
Purchase L-Tyrosine from reputable vendors who provide third-party certificates of analysis (COA). Nootropic quality varies enormously between suppliers, and contamination or mislabeling is common in unregulated markets.
N-Acetyl-L-Tyrosine (NALT) is the more bioavailable form for nootropic use. Standard L-tyrosine works but NALT is better absorbed. If you're using it to support dopamine levels after stimulant use or for ADHD support, take it on an empty stomach in the morning for best results.
Taking L-tyrosine after stimulant use to replenish dopamine precursors is a common practice, but give it a few hours after your last dose. Taking it too close to an active stimulant can potentially increase side effects since you're adding more dopamine substrate while reuptake is already being blocked.
Community Discussions (1)
See Also
References (3)
- PubChem: L-Tyrosine
PubChem compound page for L-Tyrosine (CID: 6057)
pubchem - L-Tyrosine - TripSit Factsheet
TripSit factsheet for L-Tyrosine
tripsit - L-Tyrosine - Wikipedia
Wikipedia article on L-Tyrosine
wikipedia