Isopropylphenidate

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Summary sheet: Isopropylphenidate
Isopropylphenidate
Isopropylphenidate.svg
Chemical Nomenclature
Common names Isopropylphenidate, IPH, IPPH
Substitutive name Isopropylphenidate
Systematic name Propan-2-yl 2-phenyl-2-(piperidin-2-yl)acetate
Class Membership
Psychoactive class Stimulant
Chemical class Phenidate / Piperidine
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 Common Heavy
2 - 5 - 15 - 25 - 45 mg
Light Strong
Threshold 2 - 5 mg
Light 5 - 15 mg
Common 15 - 25 mg
Strong 25 - 45 mg
Heavy 45 mg +
Duration
Total 3.5 - 6 hours
Onset 10 - 30 minutes
Come up 20 - 40 minutes
Peak 1.5 - 2.5 hours
Offset 1 - 2 hours



Insufflated
Dosage
Threshold Common Heavy
2 - 5 - 10 - 20 - 35 mg
Light Strong
Threshold 2 - 5 mg
Light 5 - 10 mg
Common 10 - 20 mg
Strong 20 - 35 mg
Heavy 35 mg +
Duration
Total 2.5 - 4 hours
Onset 2 - 5 minutes
Come up 10 - 30 minutes
Peak 1 - 2 hours
Offset 1 - 1.5 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.

Isopropylphenidate (also known as IPH, IPPH, and IPPD) is synthetic stimulant of the piperidine chemical class that produces stimulating, motivating, and focus enhancing effects when administered. It is a structural analog of the widely-prescribed ADHD medication methylphenidate and is reported to produce near identical cognitive and physical effects, albeit with less of a euphoric "rush" component and a drawn-out duration of action, properties that many find preferable for use as a study-aid or productivity enhancer.[1][2]

Isopropylphenidate has been investigated for its potential use as a replacement for methylphenidate in the treatment of ADHD and related disorders.[2] One study found that it displayed the same basic activity as a norepinephrine-dopamine reuptake inhibitor (NDRI), possessing, along with both methylphenidate and ethylphenidate, an appreciably high affinity for the dopamine transporter and effects on its cellular reuptake. It displayed comparably minor effects on norepinephrine, however, which was theorized to mean it may possess a more desirable safety and toxicity profile.[1]

Isopropylphenidate has an extremely short history of recreational use in human and has yet to be documented being sold on the streets. It was initially released following the banning of ethylphenidate, which on April 2015 became illegal in the United Kingdom following a temporary-then-permanent blanket ban. Shortly after, it became made available for sale on the online gray market as a research chemical for global distribution.

As of 2017, isopropylphenidate continues to remain available and ambiguously legal in many parts of the world, distributed almost exclusively by online research chemical vendors.

Chemistry

Isopropylphenidate is a synthetic molecule of the substituted phenethylamine and piperidine classes. It contains a phenethylamine core featuring a phenyl ring bound to an amino (NH2) group via an ethyl chain. It is structurally similar to amphetamine, featuring a substitution at Rα which is then incorporated into a piperidine ring ending at the terminal amine of the phenethylamine chain. Additionally, it contains an isopropyl acetate bound to R2 of its molecular structure, a noticeable departure from methylphenidate, which contains a methyl group in this position.

Isopropylphenidate structurally diverges from ethylphenidate and methylphenidate by the length of the carbon chain on their acetate group. Iso- regards the side chain of one carbon atom branching into two bound methyl groups, phen- indicates the phenyl ring, id- is contracted from the piperidine ring, and -ate indicates the acetate group. Isopropylphenidate is a chiral compound, and has been documented as being produced as a racemic mixture and exclusively as either of its enantiomers.[3]

Pharmacology

No formal in vivo human studies carried out using isopropylphenidate; however in vivo rat studies and in vitro studies have been performed to observe the stimulatory effects in rats, and evaluate the monoamine transporter binding affinities and affinities for various hydrolytic enzymes respectively.[1][4] The results of these studies suggest that isopropylphenidate has a very similar pharmacology to its parent compound methylphenidate, with the notable differences between the two substances being isopropylphenidate displaying significantly less activity as a norepinephrine reuptake inhibitor and the CES1 hydrolytic enzyme, which is exclusively responsible for hydrolysing both substances to ritalinic acid, having an 8 times lower affinity for isopropylphenidate compared to methylphenidate.

These differences result in the substance having more notable dopaminergic activity than adrenergic activity compared to methylphenidate at equivalent effective dosages, and in the substance having a longer duration than methylphenidate and a greater potency than methylphenidate at a given dosage. The greater potency of isopropylphenidate compared to methylphenidate is most significant with oral administration as the difference in potency is a result of the lower affinity of CES1 increasing the bioavailability of isopropylphenidate compared to methylphenidate, which is notably low for methylphenidate when administered orally due to first-pass metabolism in the liver by CES1.[5]

Despite the notable differences between the two substances, isopropylphenidate is still thought to act primarily as both a dopamine reuptake inhibitor and a norepinephrine reuptake inhibitor, meaning that it effectively boosts the levels of the norepinephrine and dopamine neurotransmitters in the brain by binding to and partially blocking the transporter proteins that normally remove those monoamines from the synaptic cleft. This allows dopamine and norepinephrine to accumulate within the brain, resulting in stimulatory effects.

Subjective effects

The effects listed below are based upon the subjective effects index and personal experiences of PsychonautWiki contributors. The listed effects should be taken with a grain of salt and will rarely (if ever) occur all at once, but heavier doses will increase the chances and are more likely to induce a full range of effects. Likewise, adverse effects become much more likely on higher doses and may include serious injury or death.

Physical effects
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After effects
Aftereffects (3).svg

Cognitive effects
User.svg

Experience reports

There are currently anecdotal reports which describe the effects of this compound within our experience index.

Additional experience reports can be found here:

Toxicity and harm potential

The toxicity and long-term health effects of recreational isopropylphenidate use do not seem to have been studied in any scientific context and the exact toxic dosage is unknown. This is because isopropylphenidate has very little history of human usage. Anecdotal evidence from people who have tried isopropylphenidate within the community suggests that there do not seem to be any negative health effects attributed to simply trying this drug at low to moderate doses by itself and using it sparingly (but nothing can be completely guaranteed). It is strongly recommended that one use harm reduction practices when using this drug.

Tolerance and addiction potential

As with other stimulants, the chronic use of isopropylphenidate can be considered moderately addictive with a high potential for abuse and is capable of causing psychological dependence among certain users. When addiction has developed, cravings and withdrawal effects may occur if a person suddenly stops their usage.

Tolerance to many of the effects of isopropylphenidate develops with prolonged and repeated use. This results in users having to administer increasingly large doses to achieve the same effects. After that, it takes about 3 - 7 days for the tolerance to be reduced to half and 1 - 2 weeks to be back at baseline (in the absence of further consumption). Isopropylphenidate presents cross-tolerance with all dopaminergic stimulants, meaning that after the consumption of isopropylphenidate all stimulants will have a reduced effect.

Psychosis

Main article: Stimulant psychosis

Abuse of compounds within the stimulant class at high dosages for prolonged periods of time can potentially result in a stimulant psychosis that may present with a variety of symptoms (e.g., paranoia, hallucinations, or delusions).[6] A review on treatment for amphetamine, dextroamphetamine, and methamphetamine abuse-induced psychosis states that about 5–15% of users fail to recover completely.[6][7] The same review asserts that, based upon at least one trial, antipsychotic medications effectively resolve the symptoms of acute amphetamine psychosis.[6]

Dangerous interactions

Although many psychoactive substances are safe to use on their own, they can become dangerous or even life-threatening when taken with other substances. The list below contains some potentially dangerous combinations, but may not include all of them. Certain combinations may be safe in low doses but still increase the possibility of injury of death. Independent research should always be conducted to ensure that a combination of two or more substances is safe before consumption.

  • 25x-NBOMe - Members of the 25x-NBOMe family are very stimulating and should not be combined with stimulants 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 - DXM should not be combined with stimulants due to its effects on serotonin and dopamine reuptake. This can lead to panic attacks, hypertensive crisis, or serotonin syndrome.
  • MXE - Combining stimulants with MXE may dangerously elevate blood pressure and increase the risk of psychosis.
  • Tramadol - Combining stimulants with tramadol increases the risk of seizures.
  • MAOIs - This combination may increase the amount of neurotransmitters such as dopamine to dangerous or even fatal levels. Examples include syrian rue, banisteriopsis caapi, 2C-T-2, 2C-T-7, αMT, and some antidepressants.[8]
  • MDMA - The neurotoxic effects of MDMA may be increased when combined with other stimulants.
  • Cocaine - This combination may increase strain on the heart.

Legality

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This legality section is a stub.

As such, it may contain incomplete or wrong information. You can help by expanding it.

  • United Kingdom - Isopropylphenidate is a class B drug in the UK as of 31st May 2017 and is illegal to possess, produce or supply. [9]

See also

External links

Literature

  • Markowitz, J. S., Zhu, H., & Patrick, K. S. (2013). Isopropylphenidate: An Ester Homolog of Methylphenidate with Sustained and Selective Dopaminergic Activity and Reduced Drug Interaction Liability. Journal of Child and Adolescent Psychopharmacology, 23(10), 648-654. https://doi.org/10.1089/cap.2013.0074
  • John S. Markowitz; Kennerly S. Patrick; Haojie Zhu (Sep 27, 2012). "Patent US20120245201 - Isopropylphenidate for Treatment of Attention-Deficit/Hyperactivity Disorder and Fatigue-Related Disorders and Conditions". Retrieved 15 August 2014.

References

  1. 1.0 1.1 1.2 1.3 Markowitz, J. S., Zhu, H., & Patrick, K. S. (2013). Isopropylphenidate: An Ester Homolog of Methylphenidate with Sustained and Selective Dopaminergic Activity and Reduced Drug Interaction Liability. Journal of Child and Adolescent Psychopharmacology, 23(10), 648-654. https://doi.org/10.1089/cap.2013.0074
  2. 2.0 2.1 John S. Markowitz; Kennerly S. Patrick; Haojie Zhu (Sep 27, 2012). "Patent US20120245201 - Isopropylphenidate for Treatment of Attention-Deficit/Hyperactivity Disorder and Fatigue-Related Disorders and Conditions". Retrieved 15 August 2014.
  3. Lachman, L., & Malspeis, L. (1962). U.S. Patent No. 3060089. Washington, DC: U.S. Patent and Trademark Office. Therapeutic lower alkyl esters of alpha-phenyl-alpha-piperidyl-(2)-acetic acid
  4. Portoghese, P. S., & Malspeis, L. (1961), Relative hydrolytic rates of certain alkyl (b) dl-α-(2-piperidyl)-phenylacetates. J. Pharm. Sci., 50: 494–501. https://doi.org/10.1002/jps.2600500611
  5. Kimko, H. C., Cross, J. T., & Abernethy, D. R. (1999). Pharmacokinetics and Clinical Effectiveness of Methylphenidate. Clinical Pharmacokinetics, 37(6), 457-470. https://doi.org/10.2165/00003088-199937060-00002
  6. 6.0 6.1 6.2 Shoptaw, S. J., Kao, U., & Ling, W. (2009). Treatment for amphetamine psychosis. The Cochrane Library. https://doi.org/10.1002/14651858.CD003026.pub3
  7. Hofmann FG (1983). A Handbook on Drug and Alcohol Abuse: The Biomedical Aspects (2nd ed.). New York: Oxford University Press. p. 329. ISBN 9780195030570.
  8. Gillman, P. K. (2005). Monoamine oxidase inhibitors, opioid analgesics and serotonin toxicity. British Journal of Anaesthesia, 95(4), 434-441. https://doi.org/10.1093/bja/aei210
  9. The Misuse of Drugs Act 1971 (Amendment) Order 2017 (Legislation.gov.uk) | http://www.legislation.gov.uk/uksi/2017/634/made