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1,4-Butanediol

Brain

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1,4-Butanediol (1,4-Butanediol; Butane-1,4-diol;1,4-Butylene glycol; Tetramethylene glycol; 110-63-4; 1,4-Dihydroxybutane; 1,4-Tetramethylene glycol; BDO; Butanediol- 1,4; 1,4-BD; 1,4-BDO; 1,4-Tetramethylene) – is an industrial chemical used in the production of industrial solvents and reagents (for example, it is used in production of spandex fibers, urethane elastomers, and copolyester ethers). It is also sometimes used recreationally because in natural environment, it turns into gamma-oxybutyrate, a drug with euphoric action, which is also a central nervous system depressant. In presence of phosphoric acid and high temperature, it is dehydrated to a solvent – tetrahydrofuran. At a temperature about 200 °C in presence of soluble ruthenium catalysts, diol undergoes dehydration resulting in the formation of butyrolactone. World-wide production of 1.4-butandiol is about one million metric tons per year, and the market price is about 2500 euros per ton. The biggest part of produced BDO is used in tetrahydrofuran (THF) production, which, in turn, is used in production of lytetramethylene glycol ester. The latter is mainly used in production of spandex fibers, elastomers, and copolyester ethers. The next largest waste is engineering plastic polybutylene terephthalate (PBT).

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Medical application of BDO is not approved, however, dimethanesulfonate (1,4-butanediol dimethanesulfonate) is available in oral and intravenous forms for treatment of chronic myeloid leukemia (Busulfan; Myleran, GlaxoSmithKline). Other names of the substance include: "BlueRaine", "Dream On", "Fubar", "Pine Needle Oil", "Rejuv@Nite", "Thunder", “Cleaner”, “Enliven”, “Inner G”, “One Comma Four", "One Four Bee", "One Four B-D-O", “Revitalize Plus”, “Serenity”, “SomatoPro”, "Soma Solution", “Sucol B”, “Thunder Nectar”, “Weight Belt Cleaner”, “White Magic”. BDO, like GBL, dissolves most types of plastic over time, so this is the reason why it is recommended to be transported and stored only in glass containers, standard gelatin capsules or high-density polyethylene. BDO has the appearance of colorless, almost odorless, waxy substance (it has either solid consistency or a consistency of oily liquid depending on temperature). It has a molecular formula C4H10O2, molecular weight of 90.12 g/mol and 246.3 g/mol (dimethylsulfonate) 202.25 g/mol (diglycidyl ether). The melting point is 20.4 degrees Celsius and the boiling point is 235 degrees Celsius.

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The most common BDO production process in the world is Reppe process by a company BASF, which involves a reaction between acetylene and formaldehyde. Acetylene reacts with two equivalents of formaldehyde, resulting in the formation of 1,4-butynediol (also known as but-2-yne- 1,4-diol). As a result of hydrogenation of 1,4-butynediol, 1,4-butanediol is formed. It is also produced on a large industrial scale by continuous hydrogenation of 2-butyne-1,4-diol with modified nickel catalysts. Single-stage flow process is carried out at a temperature of 80-16 degrees Celsius, at pressure of 300 bar. Company Mitsubishi uses a three-step process: (1) the catalytic reaction of butadiene and acetic acid yields 1,4-diacetoxy-2-butene; (2) subsequent hydrogenation gives 1,4-diacetoxybutane; and (3) hydrolysis leads to 1,4-butanediol.4. It is easily soluble in water (1.0x106 mg/L at 20 deg °C), alcohols, ketones, glycolic esters and acetates of glycolic esters; less soluble in diethyl ether and esters; it does not mix with aliphatic and aromatic hydrocarbons and chlorinated hydrocarbons. Standard screening drug tests are not able to detect BDO. Quick diagnostic method of determining 1,4-D (including GHB and GBL) level in urine by liquid chromatography-tandem mass spectrometry has been invented. In addition, there is a sensitive measurement to determine these levels in whole blood by LC– MS/MS with detection limit 0.02 mg/L for BDO in postmortem blood samples. Also, there are methods of micellar electrokinetic chromatography.

Results of The Drug Abuse Warning Network (DAWN), which is monitoring emergency room visits, associated with drug use in the USA, 1 253 956 of such visits were registered in 2004. 2 340 of the visits were associated with BDO/GHB use. In 2011, the number of cases was almost the same (2406), which indicates a low-concern stable epidemiological situation in terms of BDO abuse.

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Pharmacokinetics and Pharmacodynamics.
1,4 BDO is quickly absorbed and eliminated from the body after oral administration. The time to maximum plasma concentration is on average 24 minutes, and the elimination half-life (t1/2) is 39 ± 11 min. The main way of biotransformation is oxidation, resulting in the formation of GHB. This transformation process occurs very quickly, approximately 5 minutes after oral administration, and has a time to maximum concentration of about two minutes. After oral administration at a dose 25 mg/kg, average Cmax for GHB is 45.6 mg/L, which is 10 times higher than Cmax for BDO, i.e. 3.8 mg/L. 4 hours after administration, the level of both substances in the plasma may already be below the limit of quantification (1 mg/L). Median lethal dose of this substance was studied on rats only, and its indicators were, on average, 1,830 - 2,000 mg/kg. Initially, BDO undergoes oxidation by alcohol dehydrogenase resulting in the formation of gamma-hydroxybutyraldehyde, the intermediate aldehyde is oxidized by aldehyde dehydrogenase to GHB. Consequently, GHB is oxidized into amber semialdehyde by cytosolic and mitochondrial dehydrogenases.

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Since the enzymes responsible for BDO formation are also responsible for alcohol metabolism, alcohol can inhibit its biotransformation into GHB. This fact indicates mutual potentiating and determines an extremely high risk of developing fatal side effects when administered at high doses. In cases of acute toxicity due to 1,4-BDO, alcohol dehydrogenase inhibitor, fomepizole(4-methylpyrazol, FOM), can be an antidote, preventing GHB formation. Besides FOM, pyrazol, disulfiram, cimetidine were studied as possible inhibitors of transformation of BDO into GHB. In studies on the above topic, competitive inhibition of EtOH was revealed with constant 0m56 mM. Bioavailability after oral use was about 26%, although in studies on animals it was 50-94%. Consumption of food and carbonated drinks together with BDO reduced the time to peak plasma concentration, increased the average time to peak concentration, and reduced the area under the concentration-time curve in plasma. BDO is a colorless viscous liquid, which is produced from butane by adding alcohol groups at each end of the chain. This is one of four stable isomers of butandiol. Generally, they are endogenously present in the human body in trace amounts. BDO itself doesn't have a certain significant affinity to receptors in central nervous system, it doesn't bind to high affinity GHB-sites, GABA-A and GABA-B receptors. Due to the lack of affinity to these receptors, and also, due to BDO inactivity in terms of determination of clinical effects when used, it is considered that BDO causes its behavioral effects by transforming into GHB and by that only. Full pharmacokinetic and pharmacodynamic characteristics of GHB will be addressed in the section of the respective topic.

Clinical effects and doses.
1,4-BDO has a pronounced effect on the central nervous system. Administration of 500 mg/kg in male rats is proved to have depressing effects on сentral nervous system, characterized by narcotic sleep, reduction of reflexes and motor activity with the preservation of reactions to pain and tactile stimuli. The fundamental difference between administration of equivalent GHB doses involves the induction of sleep, the time of onset of action, the time of maximum effect and the time of falling asleep of BDO being greater than that of GHB. Also, BDO depresses motor activity, induces catalepsy and ataxia, loss of "righting reflex" to a greater extent, than GHB. One single dose of 1g/kg (for rats) by intravenous administration preserves the loss of this reflex for about 5 hours, a significant disruption in rotorod performance is observed after administration of a of dose 200 mg/kg (for rats) with absolute suppression of loco motor activity.

BDO causes pronounced and prolonged increase in average blood pressure and heart rate (studies have proven the leveling of this effect by intravenous and intracerebroventricular administration of GABA-B antagonist - CGP35348). In studies on humans at a dose of 25 mg/kg, the average maximum concentration in blood plasma with an indicator of 45 mg/l was revealed. It was reached after 39.3 minutes with elimination period of about 32 minutes. Also, in studies it was proved that continuous use of BDO causes long-term memory impairment, disruption of structures functioning at the neuronal level with a decrease in the number of neurons in the hippocampus and prefrontal cortex. People with G143A variant haplotype of the alcohol dehydrogenase gene ADH-1B have extremely slow oral clearance, the average values of which are about 160 ml/min/kg, while most people have clearance of about 450-600 ml/min/kg.

At low doses BDO acts as a psychostimulant, it mildly increases motor activity and induces a sense of cheerfulness. At higher doses (more than 1-2 ml) it acts as a sedative, promotes self-immersion, relaxation. The sedation effect is dose-dependent. Also, desirable positive effects of BDO include: reduction of anxiety; euphoria, good mood, sociability, the effect of "disinhibition", increased appreciation of music, increased libido. Negative undesirable effects include: illusions, mild hallucinations (after doses higher than 4 ml), central respiratory depression, nausea and vomiting, functional disorders of the gastrointestinal tract, dizziness, retrograde amnesia (in high doses), hypersalivation, impaired concentration and awareness.

After oral administration of the dose mentioned above, in the first 90 minutes, the effects consist of a decrease in the level of awareness and attention, dizziness, impaired concentration, euphoria, there is a slight moderate increase in average systolic and diastolic blood pressure. BDO is not a mutagenic, carcinogenic and genotoxic substance, and it does not cause clastogenicity and polyploidy (according to Irwin study on cells CHL/lU regarding this issue). As it was mentioned earlier, it is difficult to differentiate the effects of BDO from that of GHB; however, there has been more and more evidence for BDO causing physical dependence in humans, same as in rats. So, the results of the generalized data show that continuous use of BDO during 5 weeks and consequent abrupt discontinuation cause the following symptoms: discomfort and cramps in the abdomen, palpitations, tremors, spontaneous increase in blood pressure without physical exercise and the influence of exogenous factors, nystagmus, diaphoresis, mild paranoia, illusions and anxiety.

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Methods of use and doses, special instructions.
Minimal threshold dose of 1,4-BDO is 0.5 mL, which is associated with mild stimulation effects, "enlightenment ", clarity of vision, pacification, empathy. The effects are leveled in a short time without the occurrence of undesirable symptoms. Starting dose is in the range of 0.5 - 1.25 mL, which is associated with classic effects of the substance. Doses from 1.5 to 3.5 mL are considered high and the risk of undesirable side effects is high as well, sedation and euphoria are pronounced. Doses higher than 4 mL are considered extremely high and can cause sudden loss of consciousness in some people. It is not recommended using the substance earlier than 2 hours after a meal, it is recommended to take a course of proton pump inhibitors in therapeutic doses beforehand (1-2 days in advance). The onset of effects when administered orally is after 10-30 minutes, the duration of effects is about 2-4 hours. Period of post-effects can last for 1-2 days (depending on the dose, time and frequency of use of the substance).

It is strongly advised not to use BDO together with any depressants, including 2M2B, alcohol, benzodiazepines, barbiturates, GHB/GBL, methaqualone, opioids; because any combination of the sort mutually potentiates the side effects, causing central nervous system depression. This can lead to a number of negative effects up to loss of consciousness, respiratory depression and death (e.g. due to vomit aspiration). Also, it is not recommended to use BDO together with any psychostimulants because they camouflage the sedative effect of BDO, which leads to a loss of control over one's condition, associated with use. When used together with dissociative drugs, it can induce pronounced sedative effect, loss of control over one's condition and catalepsy with loss of consciousness.​
 
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